Composition and method for treating plants with exogenous chemicals

ABSTRACT

Methods and compositions are disclosed wherein exogenous chemicals are applied to plants to generate a desired biological response. One embodiment of the present invention is a plant treatment composition that comprises (a) an exogenous chemical; (b) a first excipient substance which is a compound or mixture of compounds having the formula 
     
       
         R 14 —CO—A—R 15   
       
     
     wherein R 14  is a hydrocarbyl group having about 5 to about 21 carbon atoms, R 15  is a hydrocarbyl group having 1 to about 14 carbon atoms, the total number of carbon atoms in R 14  and R 15  is about 11 to about 27, and A is O or NH; and (c) a second excipient substance which is an amphiphilic substance having a critical packing parameter greater than ⅓.

This application is a continuation of copending application Ser. No.08/957,764 filed Oct. 24, 1997, which claims the benefit of provisionalapplication serial No. 60/029,317, filed Oct. 25, 1996; provisionalapplication serial No. 60/034,887, filed Jan. 31, 1997; and provisionalapplication serial No. 60/039,789, filed Mar. 4, 1997. Each of thoseapplications is incorporated here by reference.

BACKGROUND OF THE INVENTION

This invention relates to formulations and methods for enhancing theefficacy of exogenous chemicals used in treating plants. An exogenouschemical, as defined herein, is any chemical substance, whethernaturally or synthetically derived, which (a) has biological activity oris capable of releasing in a plant an ion, moiety or derivative whichhas biological activity, and (b) is applied to a plant with the intentor result that the chemical substance or its biologically active ion,moiety or derivative enter living cells or tissues of the plant andelicit a stimulatory, inhibitory, regulatory, therapeutic, toxic orlethal response in the plant itself or in a pathogen, parasite orfeeding organism present in or on the plant. Examples of exogenouschemical substances include, but are not limited to, chemical pesticides(such as herbicides, algicides, fungicides, bactericides, viricides,insecticides, aphicides, miticides, nematicides, molluscicides, and thelike), plant growth regulators, fertilizers and nutrients, gametocides,defoliants, desiccants, mixtures thereof, and the like.

Exogenous chemicals including foliar-applied herbicides, have at timesbeen formulated with surfactants, so that when water is added, theresulting sprayable composition is more easily and effectively retainedon the foliage (e.g., the leaves or other photosynthesizing organs) ofplants. Surfactants can also bring other benefits, including improvedcontact of spray droplets with a waxy leaf surface and, in some cases,improved penetration of the accompanying exogenous chemical into theinterior of leaves. Through these and perhaps other effects, surfactantshave long been known to increase the biological effectiveness ofherbicide compositions, or other compositions of exogenous chemicals,when added to or included in such compositions. Thus, for example, theherbicide glyphosate (N-phosphonomethylglycine) has been formulated withsurfactants such as polyoxyalkylene-type surfactants including, amongother surfactants, polyoxyalkylene alkylamines. Commercial formulationsof glyphosate herbicide marketed under the trademark ROUNDUP® have beenformulated with a surfactant composition based on such a polyoxyalkylenealkylamine, in particular a polyethoxylated tallowamine, this surfactantcomposition being identified as MON 0818. Surfactants have generallybeen combined with glyphosate or other exogenous chemicals either in acommercial concentrate (herein referred to as a “coformulation”), or ina diluted mixture that is prepared from separate compositions, onecomprising an exogenous chemical (e.g. glyphosate) and anothercomprising surfactant, prior to use in the field (i.e., a tank mix).

Various combinations of exogenous chemicals and surfactants or otheradjuvants have been tested in the past. In some instances, the additionof a particular surfactant has not produced uniformly positive ornegative changes in the effect of the exogenous chemical on the plant(e.g., a surfactant that may enhance the activity of a particularherbicide on certain weeds may interfere with, or antagonize, theherbicidal efficacy on another weed species).

Some surfactants tend to degrade fairly rapidly in aqueous solutions. Asa result, surfactants that exhibit this property can only be usedeffectively in tank mixes (i.e., mixed with the other ingredients insolution or dispersion in the tank soon before spraying is to occur),rather than being coformulated in an aqueous composition with the otheringredients in the first instance. This lack of stability, or inadequateshelf-life, has hindered the use of certain surfactants in someexogenous chemical formulations.

Other surfactants, though chemically stable, are physically incompatiblewith certain exogenous chemicals, particularly in concentratecoformulations. For example, most classes of nonionic surfactant,including polyoxyethylene alkylether surfactants, do not toleratesolutions of high ionic strength, as for example in a concentratedaqueous solution of a salt of glyphosate. Physical incompatibility canalso lead to inadequate shelf-life. Other problems that can arise fromsuch incompatibility include the formation of aggregates large enough tointerfere with commercial handling and application, for example byblocking spray nozzles.

Another problem that has been observed in the past is the effect ofenvironmental conditions on uptake of an exogenous chemical compositioninto foliage of a plant. For example, conditions such as temperature,relative humidity, presence or absence of sunlight, and health of theplant to be treated, can affect the uptake of a herbicide into theplant. As a result, spraying exactly the same herbicidal composition intwo different situations can result in different herbicidal control ofthe sprayed plants.

One consequence of the above-described variability is that often ahigher rate of herbicide per unit area is applied than might actually berequired in that situation, in order to be certain that adequate controlof undesired plants will be achieved. For similar reasons, otherfoliar-applied exogenous chemicals are also typically applied atsignificantly higher rates than needed to give the desired biologicaleffect in the particular situation where they are used, to allow for thenatural variability that exists in efficiency of foliar uptake. A needtherefore exists for compositions of exogenous chemicals that, throughmore efficient uptake into plant foliage, allow reduced use rates.

Many exogenous chemicals are commercially packaged as a liquidconcentrate that contains a significant amount of water. The packagedconcentrate is shipped to distributors or retailers. Ultimately thepackaged concentrate ends up in the hands of an end user, who furtherdilutes the concentrate by adding water in accordance with labelinstructions on the package. The fully diluted material is then sprayedon plants.

A significant portion of the cost of such packaged concentrates is thecost of transporting the concentrate from the manufacturing site to thelocation where the end user purchases it. Any liquid concentrateformulation that contained relatively less water and thus more exogenouschemical would reduce the cost per unit amount of exogenous chemical.However, one important limit on the ability of the manufacturer toincrease the loading of the exogenous chemical in the concentrate is thestability of that formulation. With some combinations of ingredients, alimit will be reached at which any further reduction of water content inthe concentrate will cause it to become unstable (e.g., to separate intodiscrete layers), which may make it commercially unacceptable.

Accordingly, a need exists for improved formulations of exogenouschemicals, particularly herbicides, that are stable, effective, lesssensitive to environmental conditions, and permit the use of reducedamounts of exogenous chemical to achieve the desired biological effectin or on plants. A need also exists for stable liquid concentrateformulations of exogenous chemicals that contain less water and moreexogenous chemical than prior art concentrates.

SUMMARY OF THE INVENTION

The present invention relates to novel methods and compositions whereinexogenous chemicals are applied to plants to generate a desiredbiological response.

One embodiment of the present invention is a plant treatment compositionthat comprises (a) an exogenous chemical; (b) a first excipientsubstance which is a compound or mixture of compounds having the formula

R¹⁴—CO—A—R¹⁵  VII

wherein R¹⁴ is a hydrocarbyl group having about 5 to about 21 carbonatoms, R¹⁵ is a hydrocarbyl group having 1 to about 14 carbon atoms, thetotal number of carbon atoms in R¹⁴ and R¹⁵ is about 11 to about 27, andA is O or NH; and (c) a second excipient substance which is anamphiphilic substance having a critical packing parameter greater than⅓.

In one preferred embodiment, the weight/weight ratio of second excipientsubstance to the exogenous chemical is from about 1:3 to about 1:100. Itis particularly preferred that the weight/weight ratio of firstexcipient substance to the exogenous chemical is also from about 1:3 toabout 1:100. In another embodiment, R¹⁴ is saturated in from about 40 to100 percent by weight of all compounds having the stated formula presentin the composition. In another embodiment, R¹⁴ has about 11 to about 21carbon atoms, R¹⁵ has 1 to about 6 carbon atoms and A is O.

In certain preferred embodiments of the present invention, the firstexcipient substance is a C₁₋₄ alkyl ester of a C₁₂₋₁₈ fatty acid, morepreferably a C₁₋₄ alkyl ester of a C₁₂₋₁₈ saturated fatty acid. Propyl,isopropyl or butyl esters of C₁₂₋₁₈ fatty acids, such as butyl stearate,are especially preferred.

A wide variety of exogenous chemicals can be used in the compositionsand methods of the present invention. A preferred class isfoliar-applied exogenous chemicals, i.e. exogenous chemicals that arenormally applied post-emergence to foliage of plants. A preferredsubclass of foliar-applied exogenous chemicals is those that arewater-soluble. Especially preferred water-soluble exogenous chemicalsare those that have an anion portion and a cation portion. In oneembodiment of the invention, at least one of the anion and cationportions is biologically active and has a molecular weight of less thanabout 300. Particular examples of such exogenous chemicals where thecation portion is biologically active are paraquat, diquat andchlormequat. More commonly it is the anion portion that is biologicallyactive.

Another preferred subclass of exogenous chemicals is those that exhibitsystemic biological activity in the plant. Within this subclass, anespecially preferred group of exogenous chemicals isN-phosphonomethylglycine and its herbicidal derivatives.N-phosphonomethylglycine, often refereed to by its common nameglyphosate, can be used in its acid form, but is more preferably used inthe form of a salt. Any water-soluble salt of glyphosate can be used inthe practice of this invention. Some preferred salts include the sodium,potassium, ammonium, mono-, di-, tri- and tetra-C₁₋₄-alkylammonium,mono-, di- and tri-C₁₋₄-alkanolammonium, mono-, di- andtri-C₁₋₄-alkylsulfonium and sulfoxonium salts. The ammonium,monoisopropylammonium and trimethylsulfonium salts of glyphosate areespecially preferred. Mixtures of salts can also be useful in certainsituations.

Compositions of the present invention can be used in methods of treatingplants. Foliage of a plant is contacted with a biologically effectiveamount of the composition. “Contacting” in this context means placingthe composition on the foliage.

A composition of the present invention comprising an exogenous chemicaland a first excipient substance as described above can have a number ofdifferent physical forms. For example, the composition can furthercomprise water in an amount effective to make the composition a diluteaqueous composition ready for application to foliage of a plant.Alternatively, the composition can be a shelf-stable concentratecomposition comprising the exogenous chemical substance in an amount ofabout 10 to about 90 percent by weight. Such shelf-stable concentratescan be, for example, (1) a solid composition comprising the exogenouschemical substance in an amount of about 30 to about 90 percent byweight, such as a water-soluble or water-dispersible granularformulation, or (2) a composition that further comprises a liquiddiluent, wherein the composition comprises the exogenous chemicalsubstance in an amount of about 10 to about 60 percent by weight. Inthis latter embodiment, it is especially preferred for the exogenouschemical substance to be water-soluble and present in an aqueous phaseof the composition in an amount of about 15 to about 45 percent byweight of the composition. In this embodiment the first excipientsubstance is present predominantly in an oil phase of the composition,such composition typically being in the form of an emulsion, which canmore specifically be, for example, an oil-in-water emulsion, awater-in-oil emulsion, or a water-in-oil-in-water multiple emulsion. Inone particular embodiment of the invention, the solid or aqueouscomposition further comprises a solid inorganic particulate colloidalmaterial.

As described above, one embodiment of the invention is a sprayablecomposition that comprises an exogenous chemical, an aqueous diluent,and a first excipient substance. The term “spray composition” issometimes used herein to mean a sprayable composition.

In a related embodiment of the invention, a concentrate composition isprovided which, upon dilution, dispersion or dissolution in water formsthe sprayable composition just described. The concentrate compositioncontains a reduced amount of the aqueous diluent, or, in a particularembodiment, is a dry composition having less than 5% water by weight.Typically a concentrate composition of the invention contains at least10% by weight of the exogenous chemical, preferably at least 15%.

An alternative embodiment is a composition that does not itself comprisean exogenous chemical, but is intended for application to a plant inconjunction with or as a carrier for the application of an exogenouschemical. This composition comprises a first excipient substance and asecond excipient substance as described above. Such a composition may besprayable, in which case it also comprises an aqueous diluent, or it maybe a concentrate, requiring dilution, dispersion or dissolution in waterto provide a sprayable composition. Thus, this embodiment of theinvention can be provided as a stand-alone product and applied to aplant, diluted as appropriate with water, simultaneously with theapplication of an exogenous chemical (for example in tank mix with theexogenous chemical), or before or after the application of the exogenouschemical, preferably within about 96 hours before or after applicationof the exogenous chemical.

In all embodiments, it is believed that the second excipient substanceforms supramolecular aggregates in aqueous solution or dispersion. Inparticular it is believed that aqueous compositions of the presentinvention form aggregates in aqueous solution or dispersion the majorityof which are not simple micelles. “Majority” means that more than 50% byweight of the second excipient substance present is in the form ofcomplex aggregates other than simple micelles, e.g. as bilayers ormultilamellar structures. Preferably, more than 75% by weight is in theform of complex aggregation other than simple micelles.

Whether or not an amphiphilic substance forms such aggregates depends onits molecular architecture. The effects of molecular architecture ofsupramolecular self-assembly of amphiphilic molecules, as set forth forexample by J. N. Israelachvili, D. J. Mitchell and B. W. Ninham inFaraday Transactions II, Volume 72, pp. 1525-1568 (1976) and in numerouslater articles and monographs, are well known and understood. Animportant aspect is “critical packing parameter” (P) which is defined inthe literature by the following equation:

P=V/lA

where V is the volume of the hydrophobic tail of the molecule, l is theeffective length of the hydrophobic tail, and A is the area occupied bythe hydrophilic headgroup. These dimensions can be calculated fromphysical measurements as described in the literature and have beenpublished for numerous amphiphilic compounds.

Amphiphilic substances useful as the second excipient substance hereinhave a critical packing parameter greater than ⅓. The second excipientsubstance forms aggregates in aqueous solution or dispersion whichpreferably have at least one dimension that is greater than two timesthe molecular length of the second excipient substance.

In one embodiment of the invention, the second excipient substance is aliposome-forming material. One class of liposome-forming material is anamphiphilic compound or mixture of such compounds, preferably having twohydrophobic moieties, each of which is a saturated alkyl or acyl grouphaving from about 8 to about 22 carbon atoms. The amphiphilic compoundor mixture of such compounds having said two hydrophobic moieties withabout 8 to about 22 carbon atoms preferably constitutes from about 40 to100 percent by weight of all amphiphilic compounds having twohydrophobic moieties present in the liposome-forming material.Preferably, the liposome-forming material has a hydrophilic head groupcomprising a cationic group. More preferably, the cationic group is anamine group.

In a preferred embodiment of the invention, the second excipientsubstance comprises a liposome-forming compound having a hydrophobicmoiety comprising two independently saturated or unsaturated hydrocarbylgroups R¹ and R² each independently having about 7 to about 21 carbonatoms. A number of subclasses of such liposome-forming compounds areknown.

One subclass has the formula

N⁺(CH₂R¹)(CH₂R²)(R³)(R⁴)Z⁻  I

wherein R³ and R⁴ are independently hydrogen, C₁₋₄ alkyl or C₁₋₄hydroxyalkyl and Z is a suitable agriculturally acceptable anion.

A second subclass has the formula

N⁺(R⁵)(R⁶)(R⁷)CH₂CH(OCH₂R¹)CH₂(OCH₂R²)Z⁻  II

wherein R⁵, R⁶ and R⁷ are independently hydrogen, C₁₋₄ alkyl or C₁₋₄hydroxyalkyl and Z is a suitable anion.

A third subclass has the formula

N⁺(R⁵)(R⁶)(R⁷)CH₂CH(OCOR¹)CH₂(OCOR²)Z⁻  III

wherein R⁵, R⁶, R⁷ and Z are as defined above.

A fourth subclass has the formula

N⁺(R⁵)(R⁶)(R⁷)CH₂CH₂OPO(O⁻)OCH₂CH(OCOR¹)CH₂(OCOR²)  IV

wherein R⁵, R⁶, and R⁷ are as defined above.

Compounds of formulas I-IV will have the indicated formulas in an acidmedium, for example at a pH of 4 and may have the same formulas at otherpH's as well. It should be understood, however, that compositions of thepresent invention are not limited to use at a pH of 4.

It is preferred that about 40-100 percent of the R¹ and R² groups in thesecond excipient substance are saturated straight chain alkyl groupshaving about 7 to about 21 carbon atoms. Examples of suitableagriculturally acceptable anions Z include hydroxide, chloride, bromide,iodide, sulfate, phosphate and acetate.

In all of the above subclasses of liposome-forming substances, thehydrophilic moiety comprises a cationic group, specifically an amine orammonium group. The compound as a whole is in some cases cationic (as inI, II and III) and in some cases neutral (as in IV). Where the aminegroup is quaternary, it behaves as a cationic group independently of pH.Where the amine group is secondary or tertiary, it behaves as a cationicgroup when protonated, i.e. in an acid medium, for example at a pH of 4.

Other subclasses of liposome-forming substances having two hydrophobicchains each comprising a C₇₋₂₁ hydrocarbyl group can also be used as thesecond excipient substance in compositions of the invention. Whilesubstances having a cationic group in the hydrophilic moiety arepreferred, nonionic or anionic substances can be used if desired.

In another embodiment, the second excipient substance is a phospholipidselected from the group consisting ofdi-C₈₋₂₂-alkanoylphosphatidylcholines anddi-C₈₋₂₂-alkanoylphosphatidylethanolamines. In a particular preferredembodiment, the first excipient substance is a dipalmitoyl or distearoylester of phosphatidylcholine or a mixture thereof.

In a further embodiment of the invention, the second excipient substanceis an alkylether surfactant or mixture of such surfactants having theformula

R¹²—O—(CH₂CH₂O)_(n)(CH(CH₃)CH₂O)_(m)—R¹³  VI

wherein R¹² is an alkyl or alkenyl group having about 16 to about 22carbon atoms, n is an average number of about 10 to about 100, m is anaverage number of 0 to about 5 and R¹³ is hydrogen or C₁₋₄ alkyl. Theterm “alkylether” as used herein should be understood to includealkenylether surfactants. Preferably R¹² is a saturated straight-chainalkyl group, R¹³ is hydrogen, m is 0 and n is from about 20 to about 40.Most preferably the alkylether surfactant is a polyoxyethylene cetyl orstearyl ether or mixture thereof having 20-40 moles of ethylene oxide(EO).

Aqueous compositions of the present invention can comprisesupramolecular aggregates formed from the first and/or second excipientsubstances. In one preferred embodiment, the second excipient substanceis a vesicle-forming amphiphilic substance, such as a vesicle-forminglipid, and when the substance is dispersed in water the majority(greater than 50% by weight, preferably greater than 75% by weight) ofthe second excipient substance is present as vesicles or liposomes. Inanother preferred embodiment the second excipient substance is presentas bilayers or multilamellar structures which are not organized asvesicles or liposomes. Compositions of the present invention can alsoinclude, without limitation, colloidal systems such as emulsions(water/oil, oil/water, or multiple, e.g., water/oil/water), foams,microemulsions, and suspensions or dispersions of microparticulates,nanoparticulates, or microcapsules. Compositions of the invention caninclude more than one type of aggregate or colloidal system; examplesinclude liposomes or vesicles dispersed in a microemulsion, andcompositions having characteristics of both emulsions and suspensions,e.g. suspo-emulsions. The present invention also encompasses anyformulation, which may or may not contain a significant amount of water,that on dilution in an aqueous medium forms such colloidal systems,and/or systems comprising vesicles, liposomes, bilayers or multilamellarstructures, so long as the other requirements stipulated herein are met.

The weight ratio of each of the first and second excipient substances tothe exogenous chemical preferably is between about 1:3 and about 1:100.We have been surprised by the high level of biological effectiveness,specifically herbicidal effectiveness of a glyphosate composition,exhibited at such low ratios of such excipient substances to exogenouschemical. Higher ratios can also be effective but are likely to beuneconomic in most situations and increase the risk of producing anantagonistic effect on effectiveness of the exogenous chemical.

It is surprising that the enhancement of biological activity that hasbeen observed when using the present invention can be achieved with theaddition of relatively small amounts of such excipient substances.

In any of the above particular embodiments, the exogenous chemicaland/or first excipient substance can be encapsulated within orassociated with the aggregates (e.g., liposomes) formed by the secondexcipient substance, but do not necessarily have to be so encapsulatedor associated. “Associated” in this context means bound to or at leastpartly intercalated in some fashion in a vesicle wall, as opposed tobeing encapsulated. In yet another embodiment of the invention, theexogenous chemical and/or first excipient substance is not encapsulatedin or associated with the liposomes at all. Although the presentinvention does not exclude the possibility of so encapsulating orassociating the exogenous chemical, a presently preferred dilutesprayable liposomal composition encapsulates less than 5% by weight ofthe exogenous chemical that is present in the overall composition.Another dilute sprayable liposomal embodiment of the present inventionhas no substantial amount (i.e., less than 1% by weight) of theexogenous chemical encapsulated in the liposomes. As a droplet of such aliposomal composition dries on foliage of a plant, the proportion of theexogenous chemical that is encapsulated in the liposomes may change.

The compositions and methods of the present invention have a number ofadvantages. They provide enhanced biological activity of exogenouschemicals in or on plants in comparison with prior formulations, eitherin terms of greater ultimate biological effect, or obtaining anequivalent biological effect while using a reduced application rate ofexogenous chemical. Certain herbicide formulations of the presentinvention can avoid antagonism that has been observed in some prior artherbicide formulations, and can minimize quick production of necroticlesions on leaves that in some situations hinder overall translocationof herbicide in the plant. Certain herbicide compositions of theinvention modify the spectrum of activity of the herbicide across arange of plant species. For example, certain formulations of the presentinvention containing glyphosate can provide good herbicidal activityagainst broadleaf weeds while not losing any herbicidal effectiveness onnarrowleaf weeds. Others can enhance herbicidal effectiveness onnarrowleaf weeds to a greater extent than on broadleaf weeds. Stillothers can have enhanced effectiveness which is specific to a narrowrange of species or even a single species.

Another advantage of the present invention is that it employs relativelysmall amounts of the first and second excipient substances in relationto the amount of exogenous chemical employed. This makes thecompositions and methods of the present invention relativelyinexpensive, and also tends to reduce instability problems in specificcompositions where one or both excipient substances are physicallyincompatible with the exogenous chemical (e.g., alkylether surfactantsin solutions of high ionic strength, such as concentrated glyphosatesalt solutions).

Even at the low concentrations of the excipient substances used in thepresent invention, there may be limits on the maximum concentration ofexogenous chemical that can be used without causing compatibilityproblems (e.g., separation of the composition into discrete layers). Insome preferred embodiments of the invention, composition stability athigh loadings of exogenous chemical is maintained by adding otheringredients such as, for example, colloidal particulates. Somecompositions of the present invention exhibit enhanced biologicalactivity and have a higher loading of exogenous chemical than possiblein prior art compositions.

Further, compositions of the present invention are less sensitive insome instances to environmental conditions such as relative humidity atthe time of application to the plant. Also, the present invention allowsthe use of smaller amounts of herbicides or other pesticides, whilestill obtaining the required degree of control of weeds or otherundesired organisms.

DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS

Examples of exogenous chemical substances that can be included incompositions of the present invention include, but are not limited to,chemical pesticides (such as herbicides, algicides, fungicides,bactericides, viricides, insecticides, aphicides, miticides,nematicides, molluscicides and the like), plant growth regulators,fertilizers and nutrients, gametocides, defoliants, desiccants, mixturesthereof and the like. In one embodiment of the invention, the exogenouschemical is polar.

A preferred group of exogenous chemicals are those that are normallyapplied post-emergence to the foliage of plants, i.e. foliar-appliedexogenous chemicals.

Some exogenous chemicals useful in the present invention arewater-soluble, for example salts that comprise biologically active ions,and also comprise counterions, which may be biologically inert orrelatively inactive. A particularly preferred group of thesewater-soluble exogenous chemicals or their biologically active ions ormoieties are systemic in plants, that is, they are to some extenttranslocated from the point of entry in the foliage to other parts ofthe plant where they can exert their desired biological effect.Especially preferred among these are herbicides, plant growth regulatorsand nematicides, particularly those that have a molecular weight,excluding counterions, of less than about 300. More especially preferredamong these are exogenous chemical compounds having one or morefunctional groups selected from amine, carboxylate, phosphonate andphosphinate groups.

Among such compounds, an even more preferred group are herbicidal orplant growth, regulating exogenous chemical compounds having at leastone of each of amine, carboxylate, and either phosphonate or phosphinatefunctional groups. Salts of N-phosphonomethylglycine are examples ofthis group of exogenous chemicals. Further examples include salts ofglufosinate, for instance the ammonium salt (ammonium DL-homoalanin-4-yl(methyl) phosphinate).

Another preferred group of exogenous chemicals which can be applied bythe method of the invention are nematicides such as those disclosed inU.S. Pat. No. 5,389,680, the disclosure of which is incorporated hereinby reference. Preferred nematicides of this group are salts of3,4,4-trifluoro-3-butenoic acid or ofN-(3,4,4-trifluoro-1-oxo-3-butenyl)glycine.

Exogenous chemicals which can usefully be applied by the method of thepresent invention are normally, but not exclusively, those which areexpected to have a beneficial effect on the overall growth or yield ofdesired plants such as crops, or a deleterious or lethal effect on thegrowth of undesirable plants such as weeds. The method of the presentinvention is particularly useful for herbicides, especially those thatare normally applied post-emergence to the foliage of unwantedvegetation.

Herbicides which can be applied by the method of the present inventioninclude but are not limited to any listed in standard reference workssuch as the “Herbicide Handbook,” Weed Science Society of America, 1994,7th Edition, or the “Farm Chemicals Handbook,” Meister PublishingCompany, 1997 Edition. Illustratively these herbicides includeacetanilides such as acetochlor, alachlor and metolachlor,aminotriazole, asulam, bentazon, bialaphos, bipyridyls such as paraquat,bromacil, cyclohexenones such as clethodim and sethoxydim, dicamba,diflufenican, dinitroanilines such as pendimethalin, diphenylethers suchas acifluorfen, fomesafen and oxyfluorfen, fatty acids such as C₉₋₁₀fatty acids, fosamine, flupoxam, glufosinate, glyphosate,hydroxybenzonitriles such as bromoxynil, imidazolinones such asimazaquin and imazethapyr, isoxaben, norflurazon, phenoxies such as2,4-D, phenoxypropionates such as diclofop, fluazifop and quizalofop,picloram, propanil, substituted ureas such as fluometuron andisoproturon, sulfonylureas such as chlorimuron, chlorsulfuron,halosulfuron, metsulfuron, primisulfuron, sulfometuron andsulfosulfuron, thiocarbamates such as triallate, triazines such asatrazine and metribuzin, and triclopyr. Herbicidally active derivativesof any known herbicide are also within the scope of the presentinvention. A herbicidally active derivative is any compound which is aminor structural modification, most commonly but not restrictively asalt or ester, of a known herbicide. These compounds retain theessential activity of the parent herbicide, but may not necessarily havea potency equal to that of the parent herbicide. These compounds mayconvert to the parent herbicide before or after they enter the treatedplant. Mixtures or coformulations of a herbicide with other ingredients,or of more than one herbicide, may likewise be employed.

An especially preferred herbicide is N-phosphonomethylglycine(glyphosate), a salt, adduct or ester thereof, or a compound which isconverted to glyphosate in plant tissues or which otherwise providesglyphosate ion. Glyphosate salts that can be used according to thisinvention include but are not restricted to alkali metal, for examplesodium and potassium, salts; ammonium salt; alkylamine, for exampledimethylamine and isopropylamine, salts; alkanolamine, for exampleethanolamine, salts; alkylsulfonium, for example trimethylsulfonium,salts; sulfoxonium salts; and mixtures thereof. The herbicidalcompositions sold by Monsanto Company as ROUNDUP® and ACCORD® containthe monoisopropylamine (IPA) salt of N-phosphonomethylglycine. Theherbicidal compositions sold by Monsanto Company as ROUNDUP® Dry andRIVAL® contain the monoammonium salt of N-phosphonomethylglycine. Theherbicidal composition sold by Monsanto Company as ROUNDUP® Geoforcecontains the monosodium salt of N-phosphonomethylglycine. The herbicidalcomposition sold by Zeneca as TOUCHDOWN® contains the trimethylsulfoniumsalt of N-phosphonomethylglycine. The herbicidal properties ofN-phosphonomethylglycine and its derivatives were first discovered byFranz, then disclosed and patented in U.S. Pat. No. 3,799,758, issuedMar. 26, 1974. A number of herbicidal salts of N-phosphonomethylglycinewere patented by Franz in U.S. Pat. No. 4,405,531, issued Sep. 20, 1983.The disclosures of both of these patents are hereby incorporated byreference.

Because the commercially most important herbicidal derivatives ofN-phosphonomethylglycine are certain salts thereof, the glyphosatecompositions useful in the present invention will be described in moredetail with respect to such salts. These salts are well known andinclude ammonium, IPA, alkali metal (such as the mono-, di-, andtrisodium salts, and the mono-, di-, and tripotassium salts), andtrimethylsulfonium salts. Salts of N-phosphonomethylglycine arecommercially significant in part because they are water soluble. Thesalts listed immediately above are highly water soluble, therebyallowing for highly concentrated solutions that can be diluted at thesite of use. In accordance with the method of this invention as itpertains to glyphosate herbicide, an aqueous solution containing aherbicidally effective amount of glyphosate and other components inaccordance with the invention is applied to foliage of plants. Such anaqueous solution can be obtained by dilution of a concentratedglyphosate salt solution with water, or dissolution or dispersion inwater of a dry (e.g. granular, powder, tablet or briquette) glyphosateformulation.

Exogenous chemicals should be applied to plants at a rate sufficient togive the desired effect. These application rates are usually expressedas amount of exogenous chemical per unit area treated, e.g. grams perhectare (g/ha). What constitutes a “desired effect” varies according tothe standards and practice of those who investigate, develop, market anduse a specific class of exogenous chemicals. For example, in the case ofa herbicide, the amount applied per unit area to give 85% control of aplant species as measured by growth reduction or mortality is often usedto define a commercially effective rate.

Herbicidal effectiveness is one of the biological effects that can beenhanced through this invention. “Herbicidal effectiveness,” as usedherein, refers to any observable measure of control of plant growth,which can include one or more of the actions of (1) killing, (2)inhibiting growth, reproduction or proliferation, and (3) removing,destroying, or otherwise diminishing the occurrence and activity ofplants.

The herbicidal effectiveness data set forth herein report “inhibition”as a percentage following a standard procedure in the art which reflectsa visual assessment of plant mortality and growth reduction bycomparison with untreated plants, made by technicians specially trainedto make and record such observations. In all cases, a single technicianmakes all assessments of percent inhibition within any one experiment ortrial. Such measurements are relied upon and regularly reported byMonsanto Company in the course of its herbicide business.

The selection of application rates that are biologically effective for aspecific exogenous chemical is within the skill of the ordinaryagricultural scientist. Those of skill in the art will likewiserecognize that individual plant conditions, weather and growingconditions, as well as the specific exogenous chemical and formulationthereof selected, will affect the efficacy achieved in practicing thisinvention. Useful application rates for exogenous chemicals employed candepend upon all of the above conditions. With respect to the use of themethod of this invention for glyphosate herbicide, much information isknown about appropriate application rates. Over two decades ofglyphosate use and published studies relating to such use have providedabundant information from which a weed control practitioner can selectglyphosate application rates that are herbicidally effective onparticular species at particular growth stages in particularenvironmental conditions.

Herbicidal compositions of glyphosate or derivatives thereof are used tocontrol a very wide variety of plants worldwide. Such compositions canbe applied to a plant in a herbicidally effective amount, and caneffectively control one or more plant species of one or more of thefollowing genera without restriction: Abutilon, Amaranthus, Artemisia,Asclepias, Avena, Axonopus, Borreria, Brachiaria, Brassica, Bromus,Chenopodium, Cirsium, Commelina, Convolvulus, Cynodon, Cyperus,Digitaria, Echinochloa, Eleusine, Elymus, Equisetum, Erodium,Helianthus, Imperata, Ipomoea, Kochia, Lolium, Malva, Oryza, Ottochloa,Panicum, Paspalum, Phalaris, Phragmites, Polygonum, Portulaca,Pteridium, Pueraria, Rubus, Salsola, Setaria, Sida, Sinapis, Sorghum,Triticum, Typha, Ulex, Xanthium, and Zea.

Particularly important species for which glyphosate compositions areused are exemplified without limitation by the following:

Annual broadleaves:

velvetleaf (Abutilon theophrasti)

pigweed (Amaranthus spp.)

buttonweed (Borreria spp.)

oilseed rape, canola, indian mustard, etc. (Brassica spp.)

commelina (Commelina spp.)

filaree (Erodium spp.)

sunflower (Helianthus spp.)

morningglory (Ipomoea spp.)

kochia (Kochia scoparia)

mallow (Malva spp.)

wild buckwheat, smartweed, etc. (Polygonum spp.)

purslane (Portulaca spp.)

russian thistle (Salsola spp.)

sida (Sida spp.)

wild mustard (Sinapis arvensis)

cocklebur (Xanthium spp.)

Annual narrowleaves:

wild oat (Avena fatua)

carpetgrass (Axonopus spp.)

downy brome (Bromus tectorum)

crabgrass (Digitaria spp.)

barnyardgrass (Echinochloa crus-galli)

goosegrass (Eleusine indica)

annual ryegrass (Lolium multiflorum)

rice (Oryza sativa)

ottochloa (Ottochloa nodosa)

bahiagrass (Paspalum notatum)

canarygrass (Phalaris spp.)

foxtail (Setaria spp.)

wheat (Triticum aestivum)

corn (Zea mays)

Perennial broadleaves:

mugwort (Artemisia spp.)

milkweed (Asclepias spp.)

canada thistle (Cirsium arvense)

field bindweed (Convolvulus arvensis)

kudzu (Pueraria spp.)

Perennial narrowleaves:

brachiaria (Brachiaria spp.)

bermudagrass (Cynodon dactylon)

yellow nutsedge (Cyperus esculentus)

purple nutsedge (C. rotundus)

quackgrass (Elymus repens)

lalang (Imperata cylindrica)

perennial ryegrass (Lolium perenne)

guineagrass (Panicum maximum)

dallisgrass (Paspalum dilatatum)

reed (Phragmites spp.)

johnsongrass (Sorghum halepense)

cattail (Typha spp.)

Other perennials:

horsetail (Equisetum spp.)

bracken (Pteridium aquilinum)

blackberry (Rubus spp.)

gorse (Ulex europaeus)

Thus, the method of the present invention, as it pertains to glyphosateherbicide, can be useful on any of the above species.

Compounds useful as the first excipient substance are amides or estersof formula VII above.

R¹⁴ in formula VII is preferably aliphatic and has about 7 to about 21carbon atoms, more preferably about 13 to about 21 carbon atoms. It isespecially preferred that R¹⁴ be a saturated straight-chain alkyl group.R¹⁵ is preferably an aliphatic group having 1-6 carbon atoms, morepreferably alkyl or alkenyl having 2-4 carbon atoms. An especiallypreferred compound of formula VII for use as the first excipientsubstance is butyl stearate.

As compounds of formula VII, including butyl stearate, are generallyoily liquids, aqueous compositions containing them are typicallyemulsions having at least one aqueous phase and at least one oil phase,with the compound of formula VII being present predominantly in the oilphase. Such emulsions may be water-in-oil, oil-in-water orwater-in-oil-in-water (W/O/W) multiple emulsions.

Compositions of the present invention comprise a second excipientsubstance which is one or more amphiphilic materials, of which twoclasses are preferred.

The first class of such second excipient substances can be defined asamphiphilic liposome-forming substances. These include various lipids ofsynthetic, animal, or plant origin, including phospholipids, ceramides,sphingolipids, dialkyl surfactants, and polymeric surfactants. A varietyof these materials are known to those skilled in the art, and arecommercially available. Lecithins are particularly rich in phospholipidsand can be derived from a number of plant and animal sources. Soybeanlecithin is one particular example of a relatively inexpensivecommercially available material that includes such substances.

Many other substances have been described which can be used to formliposomes; the present invention includes compositions comprising anysuch liposome-forming substances, so long as other requirements set outabove are met, and use of such compositions for enhancing biologicaleffectiveness of exogenous chemicals applied to foliage of plants. Forexample, U.S. Pat. No. 5,580,859, incorporated here by reference,discloses liposome-forming substances having a cationic group, includingN-(2,3-di-(9-(Z)-octadecenyloxy))-prop-1-yl-N,N,N-trimethylammoniumchloride (DOTMA) and 1,2-bis(oleoyloxy)-3-(trimethylammonio)propane(DOTAP). Liposome-forming substances which are not themselves cationic,but do contain a cationic group as part of the hydrophilic moiety,include for example dioleoylphosphatidylcholine (DOPC) anddioleoylphosphatidylethanolamine (DOPE). Liposome-forming substancesthat do not contain a cationic group includedioleoylphosphatidylglycerol (DOPG). Any of these liposome-formingsubstances can be used with or without the addition of cholesterol.

These substances contain portions that are hydrophilic and hydrophobicwithin the same molecule. They have the ability to self-assemble inaqueous solution or dispersion into structures that are more complexthan simple micelles. The nature of the aggregate that will be formedcan be related to the critical packing parameter P by the followingequation:

P=V/lA

where V is the volume of the hydrophobic tail of the molecule, l is theeffective length of the hydrophobic tail, and A is the area occupied bythe hydrophilic headgroup in the surface of the aggregate. The mostprobable self-assembled structures are spherical micelles when P is lessthan ⅓, rodlike micelles when P is between ⅓ and ½, lamellar when P isbetween 1 and ½, and inverse structures when P is greater than 1. Thepreferred materials in the present invention have P greater than ⅓.

Cationic liposome-forming substances having a hydrophobic moietycomprising two hydrocarbyl chains are accompanied by a counterion(anion), identified as Z in formulas I, II and III above. Any suitableanion can be used, including agriculturally acceptable anions such ashydroxide, chloride, bromide, iodide, sulfate, phosphate and acetate. Ina specific embodiment where the exogenous chemical has a biologicallyactive anion, that anion can serve as the counterion for theliposome-forming substance. For example, glyphosate can be used in itsacid form together with the hydroxide of a cationic liposome-formingsubstance such as a compound of formula I.

Compounds of formula I known in the art to be liposome-forming includedistearyldimethylammonium chloride and bromide (also known in the art asDODAC and DODAB respectively). Compounds of formula II known in the artto be liposome-forming include DOTMA referenced above anddimyristooxypropyldimethylhydroxyethylammonium bromide (DMRIE).Compounds of formula III known in the art to be liposome-forming includedioleoyloxy-3-(dimethylammonio)propane (DODAP) and DOTAP referencedabove. Compounds of formula IV known in the art to be liposome-forminginclude DOPC and DOPE, both referenced above.

In many liposome-forming substances known in the art, the hydrophobichydrocarbyl chains are unsaturated, having one or more double bonds.Particularly commonly used in the pharmaceutical art are dioleyl ordioleoyl compounds. A potential problem with these is that in anoxidizing environment they become oxidized at the site of the doublebond. This can be inhibited by including in the formulation anantioxidant such as ascorbic acid. Alternatively the problem can beavoided by use of liposome-forming substances wherein a high proportionof the hydrophobic hydrocarbyl chains are fully saturated. Thus in apreferred embodiment of the invention. R¹ and R² in formulas I-IV areindependently saturated straight-chain alkyl groups. Particularlypreferred compositions use liposome-forming substances in which R¹ andR² are both palmityl (cetyl) or palmitoyl or, alternatively, are bothstearyl or stearoyl groups.

Phospholipids, because of their low cost and favorable environmentalproperties, are particularly favored among liposome-forming substancesin the method and compositions of the invention. Vegetable lecithins,such as soybean lecithin, have successfully been used in accordance withthe invention. The phospholipid content of the lecithin product canrange from about 10% to close to 100%. While acceptable results havebeen obtained with crude lecithin (10-20% phospholipid), it is generallypreferred to use lecithin that is at least partially de-oiled, so thatthe phospholipid content is in the region of 45%. Higher grades, such as95%, provide excellent results but the much higher cost is unlikely tobe justified for most applications.

The phospholipid component of lecithin, or any phospholipid compositionused in the present invention, may comprise one or more phosphatides ofnatural or synthetic origin. Each of these phosphatides is generally aphosphoric ester that on hydrolysis yields phosphoric acid, fattyacid(s), polyhydric alcohol and, typically, a nitrogenous base. Aphosphatide component may be present in a partially hydrolyzed form,e.g. as phosphatidic acid. Suitable phosphatides include, withoutlimitation, phosphatidylcholine, hydrogenated phosphatidylcholine,phosphatidylinositol, phosphatidylserine, phosphatidic acid,phosphatidylglycerol, phosphatidylethanolamine, N-acylphosphatidylethanolamine, and mixtures of any of these.

In vegetable lecithins a high proportion of the hydrophobic hydrocarbylchains of the phospholipid compounds are typically unsaturated. Onepreferred embodiment of compositions in accordance with the presentinvention comprises both saturated phospholipid and unsaturatedphospholipid, with the weight ratio of saturated phospholipid tounsaturated phospholipid being greater than about 1:2. In variousparticularly preferred embodiments, (1) at least 50% by weight of thephospholipids are di-C₁₂₋₂₂-saturated alkanoyl phospholipid, (2) atleast 50% by weight of the phospholipids are di-C₁₆₋₁₈-saturatedalkanoyl phospholipid, (3) at least 50% by weight of the phospholipidsare distearoyl phospholipid, (4) at least 50% by weight of thephospholipids are dipalmitoyl phospholipid, or (5) at least 50% byweight of the phospholipids are distearoyl phosphatidylcholine,dipalmitoyl phosphatidylcholine, or a mixture thereof. Higherproportions of saturated alkanoyl phospholipids are generally found inlecithins of animal origin, such as for example egg yolk lecithin, thanin vegetable lecithins.

Phospholipids are known to be chemically unstable, at least in acidmedia, where they tend to degrade to their lyso-counterparts. Thus wherephospholipids rather than more stable liposome-forming substances areused, it is usually preferable to adjust the pH of the composition. Inthe case of glyphosate compositions, the pH of a composition based on amono-salt such as the monoisopropylammonium (IPA) salt is typicallyaround 5 or lower. When phospholipids are used as the first excipientsubstance in a glyphosate composition of the invention, it willtherefore be preferable to raise the pH of the composition, for exampleto around 7. Any convenient base can be used for this purpose; it willoften be most convenient to use the same base as used in the glyphosatesalt, for example isopropylamine in the case of glyphosate IPA salt.

A second class of amphiphilic substance useful as the second excipientsubstance according to the present invention is a long-chain alkylethersurfactant having the formula VI above. R¹² can be branched orunbranched, saturated or unsaturated. R¹² is preferably straight-chainsaturated C₁₆ alkyl (cetyl) or straight-chain saturated C₁₆ alkyl(stearyl). In preferred alkylethers m is 0, n is an average number fromabout 20 to about 40 and R¹² is preferably hydrogen. Among especiallypreferred alkylether surfactants are those identified in theInternational Cosmetic Ingredient Dictionary as ceteth-20, ceteareth-20,ceteareth-27, steareth-20 and steareth-30.

Aqueous concentrate compositions in some circumstances are limited inthe degree to which an exogenous chemical such as glyphosate can beloaded. At some point, as the loading of exogenous chemical isincreased, the compositions will not remain suitably stable. This isparticularly true, for example, where the exogenous chemical isglyphosate and the second excipient substance is an alkylethersurfactant of formula VI. Addition of a small amount of colloidalparticulate to such compositions has been found to greatly increaseloading ability while retaining desired stability. Oxides of silicon,aluminum and titanium are preferred colloidal particulate materials.Particle size is preferably such that specific surface area is in therange from about 50 to about 400 m²/g. Where the exogenous chemical isglyphosate, the use of colloidal particulate enables loadings of atleast 30% by weight for compositions containing sufficient alkyletherand fatty acid ester to show enhanced herbicidal effectiveness, or atleast 40% for compositions containing alkylether but no fatty acidester, and showing herbicidal effectiveness at least equal to currentcommercial products loaded at about 30%. We have found especially usefulimprovement in storage stability can be obtained using colloidalparticulates having specific surface area between about 180 and about400 m²/g.

Other means of improving stability of highly loaded compositions mayalso be possible and are within the scope of the present invention.

Compositions in accordance with the present invention are typicallyprepared by combining water, the exogenous chemical (unless it is aformulation which will not contain an exogenous chemical) and the firstand second excipient substances. Where the second excipient substance isa liposome-forming material that requires high shear to disperse inwater, it is presently preferred to sonicate or microfluidize the secondexcipient substance in water. This can be done before or after the firstexcipient substance and/or the exogenous chemical is added. Thesonication or microfluidization will generally produce liposomes orother aggregate structures other than simple micelles. The precisenature, including average size, of liposomes or other aggregates dependsamong other things on the energy input during sonication ormicrofluidization. Higher energy input generally results in smallerliposomes. Although it is possible to entrap or otherwise bind looselyor tightly the exogenous chemical in or on liposomes or with othersupramolecular aggregates, the exogenous chemical does not need to be soentrapped or bound, and in fact the present invention is effective whenthe exogenous chemical is not entrapped or bound in the aggregates atall.

We have found for compositions of the present invention containing afatty acid ester such as butyl stearate as the first excipient substanceand lecithin as the second excipient substance, it is preferable tofirst hydrate the lecithin and then microfluidize the lecithin in watertogether with the fatty acid ester.

The concentrations of the various components will vary, in partdepending on whether a concentrate is being prepared that will befurther diluted before spraying onto a plant, or whether a solution ordispersion is being prepared that can be sprayed without furtherdilution.

In an aqueous glyphosate formulation that includes a C₁₆₋₁₈ alkylethersurfactant and butyl stearate, suitable concentrations can be:glyphosate 0.1-400 g a.e./l, alkylether surfactant 0.001-10% by weight,and butyl stearate 0.001-10% by weight. To achieve the higherconcentrations in these ranges, it will likely be found necessary to addother ingredients to provide acceptable storage stability, for examplecolloidal particulate silica or aluminum oxide at 0.5-2.5% by weight. Inan aqueous glyphosate formulation that includes a C₁₆₋₁₈ alkylethersurfactant but no butyl stearate, glyphosate concentration can suitablybe increased to 500 g a.e./l or more, in the presence of a colloidalparticulate at 0.5-2.5% by weight.

In solid glyphosate formulations, higher concentrations of ingredientsare possible because of the elimination of most of the water.

Weight/weight ratios of ingredients may be more important than absoluteconcentrations. For example, in a glyphosate formulation containinglecithin and a fatty acid ester, the ratio of lecithin to glyphosatea.e. preferably is in the range from about 1:3 to about 1:100. It isgenerally preferred to use a ratio of lecithin to glyphosate a.e. closeto as high as can be incorporated in the formulation while maintainingstability, in the presence of an amount of the fatty acid estersufficient to give the desired enhancement of herbicidal effectiveness.For example, a lecithin/glyphosate a.e. ratio in the range from about1:3 to about 1:10 will generally be found useful, although lower ratios,from about 1:10 to about 1:100, can have benefits on particular weedspecies in particular situations. The ratio of fatty acid ester toglyphosate a.e. is preferably in the range from about 1:3 to about1:100, more preferably in the lower part of this range, for example fromabout 1:10 to about 1:100.

Where the second excipient substance is an alkylether surfactant offormula VI, a suitable weight/weight ratio of alkylether surfactant toglyphosate a.e. is again in the range from about 1:3 to about 1:100,preferably from about 1:3 to about 1:10.

The ratio of fatty acid ester to second excipient substance ispreferably in the range from about 1:20 to about 5:1, more preferably inthe range from about 1:15 to about 1:1, for example around 1:10. Theranges disclosed herein can be used by one of skill in the art toprepare compositions of the invention having suitable concentrations andratios of ingredients. Preferred or optimum concentrations and ratios ofingredients for any particular use or situation can be determined byroutine experimentation.

Although the combination of the components might be done in a tank mix,it is preferred in the present invention that the combination be madefurther in advance of the application to the plant, in order to simplifythe tasks required of the person who applies the material to plants. Wehave found, however, that in some cases the biological effectiveness ofa liposome-containing composition prepared from scratch as a dilutespray composition is superior to that of a composition having the sameingredients at the same concentrations but diluted from a previouslyprepared concentrate formulation.

Although various compositions of the present invention are describedherein as comprising certain listed materials, in some preferredembodiments of the invention the compositions consist essentially of theindicated materials.

Optionally, other agriculturally acceptable materials can be included inthe compositions. For example, more than one exogenous chemical can beincluded. Also, various agriculturally acceptable adjuvants can beincluded, whether or not their purpose is to directly contribute to theeffect of the exogenous chemical on a plant. For example, when theexogenous chemical is a herbicide, liquid nitrogen fertilizer orammonium sulfate might be included in the composition. As anotherexample, stabilizers can be added to the composition. In some instancesit might be desirable to include microencapsulated acid in thecomposition, to lower the pH of a spray solution on contact with a leaf.One or more surfactants can also be included. Surfactants mentioned hereby trade name, and other surfactants that can be useful in the method ofthe invention, are indexed in standard reference works such asMcCutcheon's Emulsifiers and Detergents, 1997 edition, Handbook ofIndustrial Surfactants, 2nd Edition, 1997, published by Gower, andInternational Cosmetic Ingredient Dictionary, 6th Edition, 1995.

The compositions of the present invention can be applied to plants byspraying, using any conventional means for spraying liquids, such asspray nozzles, atomizers, or the like. Compositions of the presentinvention can be used in precision farming techniques, in whichapparatus is employed to vary the amount of exogenous chemical appliedto different parts of a field, depending on variables such as theparticular plant species present, soil composition, and the like. In oneembodiment of such techniques, a global positioning system operated withthe spraying apparatus can be used to apply the desired amount of thecomposition to different parts of a field.

The composition at the time of application to plants is preferablydilute enough to be readily sprayed using standard agricultural sprayequipment. Preferred application rates for the present invention varydepending upon a number of factors, including the type and concentrationof active ingredient and the plant species involved. Useful rates forapplying an aqueous composition to a field of foliage can range fromabout 25 to about 1,000 liters per hectare (l/ha) by spray application.The preferred application rates for aqueous solutions are in the rangefrom about 50 to about 300 l/ha.

Many exogenous chemicals (including glyphosate herbicide) must be takenup by living tissues of the plant and translocated within the plant inorder to produce the desired biological (e.g., herbicidal) effect. Thus,it is important that a herbicidal composition not be applied in such amanner as to excessively injure and interrupt the normal functioning ofthe local tissue of the plant so quickly that translocation is reduced.However, some limited degree of local injury can be insignificant, oreven beneficial, in its impact on the biological effectiveness ofcertain exogenous chemicals.

A large number of compositions of the invention are illustrated in theExamples that follow. Many concentrate compositions of glyphosate haveprovided sufficient herbicidal effectiveness in greenhouse tests towarrant field testing on a wide variety of weed species under a varietyof application conditions. Water-in-oil-in-water multiple emulsioncompositions tested in the field have included:

% w/w Fatty % in inner Type of Field Glyphos- acid Emulsi- Emulsi- aq.phase Emulsifier Emulsifier fatty acid composition ate g a.e./l esterfier #1 fier #2 Water Glyphosate #1 #2 ester F-1 100 18.0 3.0 5.0 13.820 Span 80 Tween 20 Bu stearate F-2 100 7.5 3.0 5.0 5.6 20 Span 80 Tween20 Bu stearate F-3 100 7.5 3.0 5.0 5.6 0 Span 80 Tween 20 Bu stearateF-4 160 7.5 3.0 5.0 5.6 0 Span 80 Tween 20 Bu stearate

The above compositions were prepared by process (vi) as described in theExamples.

Aqueous compositions tested in the field having a fatty acid ester asthe first excipient substance and containing a nonionic surfactant haveincluded:

Field Gly- % w/w Type of compo- phosate Fatty acid Surfac- Type fattyacid sition g a.e./l ester tant surfactant ester F-5 163 1.0 10.0oleth-20 Bu stearate F-6 163 1.0 10.0 Tween 80 Bu stearate F-7 163 1.010.0 Neodol 25-20 Bu stearate F-8 163 1.0 10.0 steareth-20 Bu stearateF-9 163 1.0 10.0 Neodol 25-12 Bu stearate F-10 105 7.5 10.0 Tween 80 Bustearate F-11 163 0.5 5.0 oleth-20 Bu stearate F-12 163 0.3 5.0 oleth-20Bu stearate F-13 163 0.3 2.5 oleth-20 Bu stearate F-14 163 1.0 10.0Neodol 25-12 Bu stearate F-15 163 0.3 5.0 Genapol UD-110 Bu stearateF-16 163 0.5 5.0 steareth-20 Bu stearate F-17 163 0.5 5.0 ceteth-20 Bustearate F-18 163 0.5 5.0 laureth-23 Bu stearate F-19 163 0.5 5.0ceteareth-27 Bu stearate F-20 163 0.5 5.0 Neodol 25-12 Bu stearate F-21163 0.5 5.0 Neodol 25-20 Bu stearate F-25 163 0.3 5.0 ceteareth-27 Bustearate F-26 163 0.3 2.5 ceteareth-27 Bu stearate F-28 163 0.5 5.0ceteareth-27 Me stearate F-29 163 0.5 5.0 steareth-20 Me stearate F-31163 0.5 5.0 Neodol 45-13 Bu stearate F-33 163 0.5 5.0 ceteareth-15 Bustearate F-35 163 0.5 5.0 steareth-30 Bu stearate

The above compositions were prepared by process (vii) as described inthe Examples.

Aqueous compositions tested in the field containing colloidalparticulates have included:

Glyphos- % w/w Type of Type of Field ate Fatty acid Surf- Colloidal Typeof colloidal fatty acid composition g a.e./l ester actant particulatesurfactant particulate ester F-36 360 1.0 10.0 1.3 steareth-20 Aerosil380 Bu stearate F-37 360 1.0 10.0 1.3 oleth-20 Aerosil 380 Bu stearateF-38 360 1.0 10.0 1.3 steareth-30 Aerosil 380 Bu stearate F-50 360 1.010.0 1.3 ceteareth-15 Aerosil 380 Bu stearate F-51 360 1.0 10.0 1.3ceteth-20 Aerosil 380 Bu stearate F-52 360 1.0 10.0 1.3 steareth-20Aerosil 380 Bu stearate F-53 360 1.0 10.0 1.3 oleth-20 Aerosil 380 Bustearate F-54 360 1.0 10.0 1.3 ceteareth-27 Aerosil 380 Bu stearate F-55360 1.0 10.0 1.3 steareth-30 Aerosil 380 Bu stearate F-60 360 1.0 10.01.3 ceteareth-27 Aerosil 380 Me stearate F-61 360 1.0 10.0 1.3ceteareth-27 Aerosil 380 Me palmitate

The above compositions were prepared by process (ix) as described in theExamples.

Aqueous compositions tested in the field having fatty acid ester as thefirst excipient substance and soybean lecithin (45% phospholipid,Avanti) as the second excipient substance have included:

% w/w Field Glyphosate MON Fatty acid Sur- Type of Type of fattycomposition g a.e./l Lecithin 0818 ester factant surfactant acid esterF-135 360 0.5 6.0 7.5 6.0 Ethomeen T/25 Bu stearate F-136 360 6.0 4.51.5 3.0 + 4.5 ceteareth-27 + Bu Stearate Ethomeen T/25 F-137 228 6.0 3.01.5 3.0 Ethomeen T/25 Bu stearate F-138 228 0.8 3.8 3.0 + 3.0ceteareth-27 + Bu stearate Ethomeen T/25 F-139 228 1.5 1.5 3.0 + 3.0ceteareth-27 + Bu stearate Ethomeen T/25 F-140 228 6.7 0.8 0.7 0.8Ethomeen T/25 Bu stearate F-141 228 6.7 1.7 0.7 1.7 Ethomeen T/25 Bustearate F-142 228 6.7 3.3 0.7 3.3 Ethomeen T/25 Bu stearate F-143 2283.3 0.8 0.7 0.8 Ethomeen T/25 Bu stearate F-144 228 3.3 1.7 0.7 1.7Ethomeen T/25 Bu stearate F-145 228 3.3 2.5 0.7 2.5 Ethomeen T/25 Bustearate F-146 228 3.3 3.3 0.7 3.3 Ethomeen T/25 Bu stearate F-147 2286.7 2.5 0.7 2.5 Ethomeen T/25 Bu stearate F-148 228 3.0 0.5 3.0 EthomeenT/25 Bu stearate F-149 228 2.0 2.5 0.5 2.5 Ethomeen T/25 Bu stearateF-150 228 4.0 6.0 0.5 Bu stearate F-151 228 4.0 6.0 2.0 Bu stearateF-152 228 4.0 6.0 1.0 Bu stearate F-153 228 2.0 2.0 0.5 Bu stearateF-154 228 2.0 4.0 0.5 Bu stearate F-155 228 6.0 0.5 Bu stearate

The above compositions were prepared by process (x) as described in theExamples.

Dry compositions tested in the field have included:

% w/w Field Glyphos- Butyl Surfact- Colloidal Type of Type ofcomposition ate a.e. Lecithin stearate ant particulate surfactantcolloidal particulate F-164 64 12.0 3.0 12.0 MON 0818 F-165 64 6.7 6.713.2 MON 0818 F-167 66 2.0 20.0 2.0 steareth-20 Aerosil blend 1 F-169 662.0 20.0 2.0 oleth-20 Aerosil blend 1 F-170 66 2.0 20.0 2.0 ceteareth-27Aerosil blend 1 Aerosil blend 1: Aerosil MOX-80 + Aerosil MOX-170 (1:1)

The above compositions were prepared by the process described for drygranular compositions in the Examples.

EXAMPLES

In the following Examples illustrative of the invention, greenhousetests were conducted to evaluate relative herbicidal effectiveness ofglyphosate compositions. Compositions included for comparative purposesincluded the following:

Formulation B: which consists of 41% by weight of glyphosate IPA salt inaqueous solution. This formulation is sold in the USA by MonsantoCompany under the ACCORD® trademark.

Formulation C: which consists of 41% by weight of glyphosate IPA salt inaqueous solution with a coformulant (15% by weight) of a surfactant (MON0818 of Monsanto Company) based on polyoxyethylene (15) tallowamine.This formulation is sold in Canada by Monsanto Company under theROUNDUP® trademark.

Formulation J: which consists of 41% by weight of glyphosate IPA salt inaqueous solution, together with surfactant. This formulation is sold inthe USA by Monsanto Company under the ROUNDUP® ULTRA trademark.

Formulation K: which consists of 75% by weight of glyphosate ammoniumsalt together with surfactant, as a water-soluble dry granularformulation. This formulation is sold in Australia by Monsanto Companyunder the ROUNDUP® DRY trademark.

Formulations B, C and J contain 356 grams of glyphosate acid equivalentper liter (g a.e./l). Formulation K contains 680 grams of glyphosateacid equivalent per kilogram (g a.e./kg).

Various proprietary excipients were used in compositions of theExamples. They may be identified as follows:

Trade name Manufacturer Chemical description Aerosil 90 Degussaamorphous silica, 90 m²/g Aerosil 380 Degussa amorphous silica, 380 m²/gAerosil MOX-80 Degussa amorphous silica/aluminum oxide, 80 m²/g AerosilMOX-170 Degussa amorphous silica/aluminum oxide, 170 m²/g Aerosil OX-50Degussa amorphous silica, 50 m²/g Aerosil R-202 Degussa amorphoushydrophobic silica (dimethylsiloxane surface group) Aerosil R-805Degussa amorphous hydrophobic silica (octyl surface group) Aerosil R-812Degussa amorphous hydrophobic silica (trimethylsilyl surface group)Aerosol OT Cytec dioctyl sulfosuccinate, Na salt Agrimer AL-25 ISP1-ethenyl hexadecyl-2-pyrrolidinone Agrimer AL-30 ISP1-ethenyl-2-pyrrolidinone polymer Aluminum oxide C Degussa aluminumoxide, 100 m²/g Arcosolve DPM Arco dipropyleneglycol monomethyl etherDowanol PNB Dow propylene glycol n-butyl ether Dowanol TPNB Dowtripropylene glycol n-butyl ether Emerest 2421 Henkel glyceryl oleateEmerest 2661 Henkel PEG-12 laurate Emid 6545 Henkel oleic diethanolamideEthomeen C/12 Akzo cocoamine 2EO Ethomeen T/12 Akzo tallowamine 2EOEthomeen T/25 Akzo tallowamine 15EO Exxate 700 Exxon C₇ alkyl acetateExxate 1000 Exxon C₇ alkyl acetate Exxol D-130 Exxon dearomatizedaliphatic solvent Fluorad FC-135 3M fluorinated alkyl quaternaryammonium iodide Fluorad FC-754 3M fluorinated alkyl quaternary ammoniumchloride Genapol UD-110 Roechst C₁₁ oxo alcohol 11EO Isopar V Exxonisoparaffinic oil MON 0818 Monsanto tallowamine 15EO-based surfactantMyrj 52 ICI PEG-40 stearate Myrj 59 ICI PEG-100 stearate Neodol 1-7Shell C₁₁ linear alcohol 7EO Neodol 1-9 Shell C₁₁ linear alcohol 9EONeodol 25-12 Shell C₁₁₋₁₅ linear alcohol 12EO Neodol 25-20 Shell C₁₁₋₁₅linear alcohol 20EO Neodol 25-3 Shell C₁₁₋₁₅ linear alcohol 3EO Neodol25-9 Shell C₁₁₋₁₅ linear alcohol 9EO Neodol 45-13 Shell C₁₃₋₁₅ linearalcohol 13EO Neodol 91-2.5 Shell C₉₋₁₁ linear alcohol 2.5EO Orchex 796Exxon paraffinic oil Pluronic F-108 BASF 128EO-54PO-128EO blockcopolymer Pluronic F-127 BASF 98EO-67PO-98EO block copolymer PluronicF-68 BASF 75EO-30PO-75EO block copolymer Pluronic L-43 BASF 7EO-21PO-7EOblock copolymer Pluronic L-81 BASF 6EO-39PO-6EO block copolymer PluronicP-84 BASF 27EO-39PO-27EO block copolymer Silwet 800 Witcoheptamethyltrisiloxane EO Silwet L-77 Witco heptamethyltrisiloxane 7EOmethyl ether Span 60 ICI sorbitan monostearate Span 65 ICI sorbitantristearate Span 80 ICI sorbitan monooleate Span 85 ICI sorbitantrioleate Surfynol 104 Air Products tetramethyldecyne diol Tergitol15-S-15 Union Carbide C₁₅ branched secondary alcohol 15EO Tergitol15-S-20 Union Carbide C₁₅ branched secondary alcohol 20EO Tergitol15-S-30 Union Carbide C₁₅ branched secondary alcohol 30EO Tergitol15-S-40 Union Carbide C₁₅ branched secondary alcohol 40EO Toximul 8240Stepan PEG-36 castor oil Tween 20 ICI sorbitan monolaurate 20EO Tween 40ICI sorbitan monopalmitate 20EO Tween 80 ICI sorbitan monooleate 20EOTween 85 ICI sorbitan trioleate 20EO

Fluorad FC-135, though defined only generically as above in 3M productliterature and in standard directories, has been specifically identifiedas

 C₈F₁₇SO₂NH(CH₂)₃N⁺(CH₃)₃ I⁻

in a paper by J. Linert & J. N. Chasman of 3M, titled “The effects offluorochemical surfactants on recoatability” in the Dec. 20, 1993 issueof American Paint & Coatings Journal, and reprinted as a trade brochureby 3M. Fluorad FC-754 is believed to have the structure

C₈F₁₇SO₂NH(CH₂)₃N⁺(CH₃)₃ Cl⁻

that is, identical to Fluorad FC-135 but with a chloride anion replacingiodide.

Fatty alcohol ethoxylate surfactants are referred to in the Examples bytheir generic names as given in the International Cosmetic IngredientDictionary, 6th Edition, 1995 (Cosmetic, Toiletry and FragranceAssociation, Washington, DC). They were interchangeably sourced fromvarious manufacturers, for example:

Laureth-23: Brij 35 (ICI), Trycol 5964 (Henkel).

Ceteth-10: Brij 56 (ICI).

Ceteth-20: Brij 58 (ICI).

Steareth-10: Brij 76 (ICI).

Steareth-20: Brij 78 (ICI), Emthox 5888-A (Henkel), STA-20 (Heterene).

Steareth-30: STA-30 (Heterene).

Steareth-100: Brij 700 (ICI).

Ceteareth-15: CS-15 (Heterene).

Ceteareth-20: CS-20 (Heterene).

Ceteareth-27: Plurafac A-38 (BASF).

Ceteareth-55: Plurafac A-39 (BASF).

Oleth-2: Brij 92 (ICI).

Oleth-10: Brij 97 (ICI).

Oleth-20: Brij 98 (ICI), Trycol 5971 (Henkel).

Where a proprietary excipient is a surfactant supplied as a solution inwater or other solvent, the amount to be used was calculated on a truesurfactant basis, not an “as is” basis. For example, Fluorad FC-135 issupplied as 50% true surfactant, together with 33% isopropanol and 17%water; thus to provide a composition containing 0.1% w/w Fluorad FC-135as reported herein, 0.2 g of the product as supplied was included in 100g of the composition. The amount of lecithin, however, is alwaysreported herein on an “as is” basis, regardless of the content ofphospholipid in the lecithin sample used.

Spray compositions of the Examples contained an exogenous chemical, suchas glyphosate IPA salt, in addition to the excipient ingredients listed.The amount of exogenous chemical was selected to provide the desiredrate in grams per hectare (g/ha) when applied in a spray volume of 93l/ha. Several exogenous chemical rates were applied for eachcomposition. Thus, except where otherwise indicated, when spraycompositions were tested, the concentration of exogenous chemical variedin direct proportion to exogenous chemical rate, but the concentrationof excipient ingredients was held constant across different exogenouschemical rates.

Concentrate compositions were tested by dilution, dissolution ordispersion in water to form spray compositions. In these spraycompositions prepared from concentrates, the concentration of excipientingredients varied with that of exogenous chemical.

For spray compositions of the Examples, unless otherwise indicated, thepreparation procedure was one of the following processes (i) to (iii).

(i) For compositions not containing lecithin or phospholipids, aqueouscompositions were prepared by simple mixing of ingredients under mildagitation.

(ii) A weighed quantity of lecithin in powder form was dissolved in 0.4ml chloroform in a 100 ml bottle. The resulting solution was air-driedto leave a thin film of lecithin, to which was added 30 ml deionizedwater. The bottle and its contents were then sonicated in a Fisher SonicDismembrator, Model 550, fitted with a 2.4 cm probe tip, set at outputlevel 8, and operated continuously for 3 minutes. The resulting aqueousdispersion of lecithin was then allowed to cool to room temperature, andformed a lecithin stock which was later mixed in the required amountswith other ingredients under mild agitation. In some cases, as indicatedin the Examples, certain ingredients were added to the lecithin in waterbefore sonication, so that the lecithin and these ingredients weresonicated together. Without being bound by theory, it is believed thatby sonicating a formulation ingredient together with lecithin, at leastsome of that ingredient becomes encapsulated within, or otherwise boundto or trapped by, vesicles or other aggregates formed by phospholipidspresent in the lecithin.

(iii) The procedure of process (ii) was followed except that, beforesonication, the step of forming a lecithin solution in chloroform wasomitted. Instead, lecithin in powder form was placed in a beaker, waterwas added and the beaker and its contents were then sonicated.

For concentrate compositions of the Examples containing lecithin, thepreparation procedure was one of the following processes (iv) or (v), orin some cases process (x) below.

(iv) A weighed amount of lecithin powder of the type indicated wasplaced in a beaker and deionized water was added in no more than theamount required for the desired final composition. The beaker and itscontents were then placed in a Fisher Sonic Dismembrator, Model 550,fitted with a 2.4 cm probe tip, set at output level 8, and operated for5 minutes. The resulting lecithin dispersion formed the basis to whichother ingredients were added with mild agitation to make the aqueousconcentrate formulation. The order of addition of these ingredients wasvaried and was sometimes found to affect the physical stability of theconcentrate formulation. Where a fluoro-organic surfactant such asFluorad FC-135 or FC-754 was to be included, it was generally addedfirst, followed by other surfactants if required and then by theexogenous chemical. Where the exogenous chemical used was glyphosate IPAsalt, this was added in the form of a 62% (45% a.e.) solution by weight,at a pH of 4.4 to 4.6. A final adjustment with water took place ifnecessary as the last step. In some cases certain ingredients of theconcentrate formulation were added before rather than after sonication,so that they were sonicated with the lecithin.

(v) A weighed amount of lecithin powder of the type indicated was placedin a beaker and deionized water was added in sufficient quantity toprovide, after sonication as detailed below, a lecithin stock at aconvenient concentration, normally in the range from 10% to 20% w/w andtypically 15% w/w. The beaker and its contents were then placed in aFisher Sonic Dismembrator, Model 550, fitted with a 2.4 cm probe tipwith the pulse period set at 15 seconds with 1 minute intervals betweenpulses to allow cooling. Power output was set at level 8. After a totalof 3 minutes of sonication (12 pulse periods) the resulting lecithinstock was finally adjusted to the desired concentration if necessarywith deionized water. To prepare an aqueous concentrate formulation, thefollowing ingredients were mixed in the appropriate proportions withmild agitation, normally in the order given although this was sometimesvaried and was found in some cases to affect the physical stability ofthe concentrate formulation: (a) exogenous chemical, for exampleglyphosate IPA salt as a 62% w/w solution at pH 4.4-4.6; (b) lecithinstock; (c) other ingredients if required; and (d) water.

Many of the Examples feature aqueous concentrate compositions of theinvention. Except where otherwise indicated, these aqueous concentratecompositions were prepared by the following general processes (vi) to(ix).

(vi) Water-in-oil-in-water (W/O/W) multiple emulsions were prepared asfollows. First a water-in-oil emulsion was prepared. To do this, therequired amounts of the selected oil and a first emulsifier (referred toin the Examples as “emulsifier #1”) were mixed thoroughly. If it wasdesired to prepare the formulation with glyphosate in the inner aqueousphase, a measured amount of concentrated (62% w/w) aqueous solution ofglyphosate IPA salt was added to the mixture of oil and first emulsifierwith agitation to ensure homogeneity. The amount of water required inthe inner aqueous phase was then added to complete the water-in-oilemulsion, which was finally subjected to high-shear mixing, typicallyusing a Silverson L4RT-A mixer fitted with a fine emulsor screenoperated for 3 minutes at 10,000 rpm. The required amount of a secondemulsifier (referred to in the Examples as “emulsifier #2”) was nextadded to the water-in-oil emulsion with agitation to ensure homogeneity.If it was desired to prepare the formulation with glyphosate in theouter aqueous phase, a measured amount of concentrated (62% w/w) aqueoussolution of glyphosate IPA salt was added to the blend of thewater-in-oil emulsion and the second emulsifier with further agitation.To complete the water-in-oil-in-water multiple emulsion composition, theamount of water required in the outer aqueous phase was added. Thecomposition was finally subjected to high-shear mixing, typically usinga Silverson L4RT-A mixer fitted with a medium emulsor screen, operatedfor 3 minutes at 7,000 rpm.

(vii) Oil-in-water (O/W) emulsions were prepared as follows. Therequired amount of the selected oil and surfactant (sometimes referredto in the Examples as “emulsifier #2” as it corresponds to the secondemulsifier in process (vi)) were mixed thoroughly. If the surfactantselected was not free-flowing at ambient temperature, heat was appliedto bring the surfactant into a flowable condition before mixing with theoil. A measured amount of concentrated (62% w/w) aqueous solution ofglyphosate IPA salt was added to the surfactant-oil mixture withagitation. The required amount of water was added to bring theconcentration of glyphosate and other ingredients to the desired level.The composition was finally subjected to high-shear mixing, typicallyusing a Silverson L4RT-A mixer fitted with a medium emulsor screen,operated for 3 minutes at 7,000 rpm.

(viii) Surfactant-containing aqueous solution concentrates having no oilcomponent were prepared as follows. A concentrated (62% w/w) aqueoussolution of glyphosate IPA salt was added in the desired amount to aweighed quantity of the selected surfactant(s). If the surfactantselected is not free-flowing at ambient temperature, heat was applied tobring the surfactant into a flowable condition before adding theglyphosate solution. The required amount of water was added to bring theconcentration of glyphosate and other ingredients to the desired level.The composition was finally subjected to high-shear mixing, typicallyusing a Silverson L4RT-A mixer fitted with a medium emulsor screen,operated for 3 minutes at 7,000 rpm.

(ix) For compositions containing a colloidal particulate, the requiredamount by weight of the selected colloidal particulate was suspended ina concentrated (62% w/w) aqueous solution of glyphosate IPA salt andagitated with cooling to ensure homogeneity. To the resulting suspensionwas added the required amount by weight of the selected surfactant(s).For a surfactant which is not free-flowing at ambient temperature, heatwas applied to bring the surfactant into a flowable condition beforeadding it to the suspension. In those instances where an oil, such asbutyl stearate, was also to be included in the composition, the oil wasfirst thoroughly mixed with the surfactant and the surfactant-oilmixture added to the suspension. To complete the aqueous concentrate,the required amount of water was added to bring the concentration ofglyphosate and other ingredients to the desired level. The concentratewas finally subjected to high-shear mixing, typically using a SilversonL4RT-A mixer fitted with a medium emulsor screen, operated for 3 minutesat 7,000 rpm.

(x) The procedure for preparing aqueous concentrate formulationscontaining lecithin and butyl stearate was different from that followedfor other lecithin-containing concentrates. Exogenous chemical, forexample glyphosate IPA salt, was first added, with mild agitation, todeionized water in a formulation jar. The selected surfactant (otherthan lecithin) was then added, while continuing the agitation, to form apreliminary exogenous chemical/surfactant mixture. Where the surfactantis not free-flowing at ambient temperature, the order of addition wasnot as above. Instead, the non-free-flowing surfactant was first addedto water together with any other surfactant (other than lecithin)required in the composition, and was then heated to 55° C. in a shakerbath for 2 hours. The resulting mixture was allowed to cool, thenexogenous chemical was added with mild agitation to form the preliminaryexogenous chemical/surfactant mixture. A weighed amount of the selectedlecithin was added to the preliminary exogenous chemical/surfactantmixture, with stirring to break up lumps. The mixture was left for about1 hour to allow the lecithin to hydrate, then butyl stearate was added,with further stirring until no phase separation occurred. The mixturewas then transferred to a microfluidizer (Microfluidics InternationalCorporation, Model M-110F) and microfluidized for 3 to 5 cycles at10,000 psi (69 MPa). In each cycle, the formulation jar was rinsed withmicrofluidized mixture. In the last cycle, the finished composition wascollected in a clean dry beaker.

The following procedure was used for testing compositions of theExamples to determine herbicidal effectiveness, except where otherwiseindicated.

Seeds of the plant species indicated were planted in 85 mm square potsin a soil mix which was previously steam sterilized and prefertilizedwith a 13-13-14 NPK slow release fertilizer at a rate of 3.6 kg/m³. Thepots were placed in a greenhouse with sub-irrigation. About one weekafter emergence, seedlings were thinned as needed, including removal ofany unhealthy or abnormal plants, to create a uniform series of testpots.

The plants were maintained for the duration of the test in thegreenhouse where they received a minimum of 14 hours of light per day.If natural light was insufficient to achieve the daily requirement,artificial light with an intensity of approximately 475 microeinsteinswas used to make up the difference. Exposure temperatures were notprecisely controlled but averaged about 27° C. during the day and about18° C. during the night. Plants were sub-irrigated throughout the testto ensure adequate soil moisture levels.

Pots were assigned to different treatments in a fully randomizedexperimental design with 3 replications. A set of pots was leftuntreated as a reference against which effects of the treatments couldlater be evaluated.

Application of glyphosate compositions was made by spraying with a tracksprayer fitted with a 9501E nozzle calibrated to deliver a spray volumeof 93 liters per hectare (l/ha) at a pressure of 166 kilopascals (kPa).After treatment, pots were returned to the greenhouse until ready forevaluation.

Treatments were made using dilute aqueous compositions. These could beprepared as spray compositions directly from their ingredients, or bydilution with water of preformulated concentrate compositions.

For evaluation of herbicidal effectiveness, all plants in the test wereexamined by a single practiced technician, who recorded percentinhibition, a visual measurement of the effectiveness of each treatmentby comparison with untreated plants. Inhibition of 0% indicates noeffect, and inhibition of 100% indicates that all of the plants arecompletely dead. Inhibition of 85% or more is in most cases consideredacceptable for normal herbicidal use; however in greenhouse tests suchas those of the Examples it is normal to apply compositions at rateswhich give less than 85% inhibition, as this makes it easier todiscriminate among compositions having different levels ofeffectiveness.

Example 1

Invert (water-in-oil) emulsion formulations containing glyphosate IPAsalt were prepared as follows. In 235 g of a selected oil, 15 g soybeanlecithin (20% phospholipid, Avanti) was dissolved to provide an oilfeedstock. To a weighed amount of the oil feedstock in a Waring blender,a small quantity of concentrated (62% w/w) aqueous solution ofglyphosate IPA salt was added quickly under high shear to make aready-to-spray water-in-oil emulsion. The precise quantity of oilfeedstock and glyphosate salt solution varied depending on the desiredapplication rate. For a glyphosate rate of 100 g a.e./ha in a sprayvolume of 93 l/ha, 0.12 g glyphosate salt solution was added to 49.9 goil feedstock. For higher rates, the amount of glyphosate salt solutionwas increased pro rata and the total weight of emulsion prepared keptconstant at 50 g. Table 1a shows the composition of the oil feedstocksused.

TABLE 1a Oil feedstock % w/w Type of no. Oil Lecithin oil 1-01 94.0 6.0mineral oil 1-02 94.0 6.0 methyl oleate 1-03 94.0 6.0 silicone oil

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 14 days after planting ABUTH and 17 days after planting ECHCF.Evaluation of herbicidal inhibition was done 19 days after application.

Formulation C was applied in 93 l/ha of aqueous spray solution as acomparative treatment. Results, averaged for all replicates of eachtreatment, are shown in Table 1b.

TABLE 1b Glyphosate rate % Inhibition Spray composition g a.e./ha ABUTHECHCF Formulation C 100 40 65 300 80 83 400 93 89 500 99 95 1-01 +glyphosate IPA salt  0 20 0 100 0 0 300 10 11 400 8 0 500 5 10 1-02 +glyphosate IPA salt  0 8 0 100 30 3 300 25 3 400 38 3 500 20 13 1-03 +glyphosate IPA salt  0 0 0 100 3 6 300 48 0 400 5 0 500 25 0

Water-in-oil emulsion compositions of this Example did not show a highdegree of herbicidal effectiveness.

Example 2

Aqueous spray compositions were prepared containing glyphosate IPA saltand excipient ingredients as shown in Table 2a. Process (iii) wasfollowed for all compositions, using soybean lecithin (20% phospholipid,Avanti).

TABLE 2a Spray % w/w Components compo- Lecithin Fluorad Silwet MethylSodium sonicated with sition g/l FC-135 L-77 caprate cholate lecithin2-01 5.0 none 2-02 5.0 0.50 none 2-03 5.0 0.50 L-77 2-04 2.5 none 2-050.5 none 2-06 2.5 0.50 none 2-07 2.5 0.50 L-77 2-08 0.5 0.50 none 2-090.5 0.50 L-77 2-10 2.5 0.25 none 2-11 2.5 0.10 none 2-12 2.5 0.05 none2-13 0.5 0.25 none 2-14 0.5 0.10 none 2-15 0.5 0.05 none 2-16 2.5 0.10Me caprate 2-17 2.5 0.10 Na cholate

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 18 days after planting ABUTH and 21 days after planting ECHCF, andevaluation of herbicidal inhibition was done 18 days after application.

In addition to compositions 2-01 to 2-17, spray compositions wereprepared by tank mixing Formulations B and C with Fluorad FC-135 atvarious concentrations. Formulations B and C, alone and tank mixed with0.5% Silwet L-77, were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 2b.

TABLE 2b Glyphosate rate % Inhibition Spray composition g a.e./ha ABUTHECHCF Formulation B 200 53 69 300 76 85 400 77 81 Formulation B + 200100 28 Silwet L-77 0.5% v/v 300 100 35 400 100 47 Formulation C 200 5781 300 73 90 400 98 94 Formulation C + 200 99 28 Silwet L-77 0.5% v/v300 98 53 400 99 56 Formulation B + 200 76 85 Fluorad FC-135 0.25% w/v300 95 81 400 100 100 Formulation B + 200 77 70 Fluorad FC-135 0.1% w/v300 94 81 400 98 87 Formulation B + 200 65 73 Fluorad FC-135 0.05% w/v300 84 94 400 88 96 Formulation C + 200 83 78 Fluorad FC-135 0.25% w/v300 98 94 400 97 95 Formulation C + 200 65 66 Fluorad FC-135 0.1% w/v300 89 86 400 97 89 Formulation C + 200 70 78 Fluorad FC-135 0.05% w/v300 79 84 400 96 98 2-01 200 93 71 300 91 89 400 97 97 2-02 200 95 59300 97 68 400 99 79 2-03 200 97 55 300 98 62 400 100 76 2-04 200 83 72300 87 84 400 95 100 2-05 200 69 78 300 92 93 400 98 97 2-06 200 94 61300 99 67 400 100 76 2-07 200 99 52 300 99 63 400 100 80 2-08 200 96 47300 99 57 400 99 55 2-09 200 99 23 300 98 58 400 100 53 2-10 200 89 91300 91 99 400 98 100 2-11 200 81 91 300 91 99 400 92 100 2-12 200 66 96300 86 100 400 94 99 2-13 200 80 97 300 98 98 400 99 100 2-14 200 68 92300 89 100 400 99 98 2-15 200 84 95 300 94 100 400 97 100 2-16 200 73 94300 89 100 400 99 100 2-17 200 58 94 300 77 96 400 90 90

In this test addition of 0.1% methyl caprate to 0.25% lecithin, themethyl caprate being sonicated together with the lecithin, enhancedperformance on ECHCF but not on ABUTH (compare compositions 2-16 and2-04).

Example 3

Compositions 2-01 to 2-17 of Example 2, and tank mixtures ofFormulations B and C with Fluorad FC-135, were tested in this Example.Prickly sida (Sida spinosa, SIDSP) plants were grown and treated by thestandard procedure given above. Applications of spray compositions weremade 22 days after planting SIDSP, and evaluation of herbicidalinhibition was done 19 days after application.

Formulations B and C, alone and tank mixed with 0.5% Silwet L-77, wereapplied as comparative treatments. Results, averaged for all replicatesof each treatment, are shown in Table 3.

TABLE 3 Glyphosate rate % Inhibition Spray composition g a.e./ha SIDSPFormulation B 200 46 300 75 400 80 Formulation B + 200 96 Silwet L-770.5% v/v 300 89 400 87 Formulation C 200 80 300 98 400 98 FormulationC + 200 75 Silwet L-77 0.5% v/v 300 91 400 94 Formulation B + 200 82Fluorad FC-135 0.25% w/v 300 94 400 98 Formulation B + 200 70 FluoradFC-135 0.1% w/v 300 93 400 88 Formulation B + 200 79 Fluorad FC-1350.05% w/v 300 92 400 99 Formulation C + 200 79 Fluorad FC-135 0.25% w/v300 97 400 97 Formulation C + 200 90 Fluorad FC-135 0.1% w/v 300 96 40097 Formulation C + 200 80 Fluorad FC-135 0.05% w/v 300 96 400 99 2-01200 93 300 97 400 98 2-02 200 71 300 89 400 89 2-03 200 71 300 87 400 982-04 200 76 300 100 400 100 2-05 200 91 300 99 400 97 2-06 200 57 300 95400 88 2-07 200 64 300 68 400 94 2-08 200 89 300 96 400 99 2-09 200 80300 77 400 94 2-10 200 90 300 94 400 98 2-11 200 81 300 100 400 96 2-12200 86 300 92 400 95 2-13 200 86 300 99 400 100 2-14 200 97 300 100 400100 2-15 200 99 300 100 400 100 2-16 200 92 300 100 400 100 2-17 200 92300 99 400 100

Herbicidal effectiveness of Formulation C was very high on SIDSP in thistest and accordingly enhancements are difficult to discern. However,0.1% methyl caprate (composition 2-16) enhanced the effectiveness of acomposition containing 0.25% lecithin (2-04).

Example 4

Aqueous spray compositions were prepared containing glyphosate IPA saltand excipient ingredients as shown in Table 4a. Process (iii) wasfollowed for all compositions, using soybean lecithin (20% phospholipid,Avanti).

TABLE 4a Spray Lecithin % w/w (*) Other Components comp. g/l FC-135Other (*) ingredient sonicated with lecithin 4-01 2.5 none 4-02 2.5glyphosate 4-03 2.5 0.25 none 4-04 2.5 0.25 glyphosate 4-05 2.5 0.25Silwet 800 none 4-06 2.5 0.25 Silwet 800 Silwet 800 4-07 2.5 0.25 Silwet800 Silwet, glyphosate 4-08 0.5 none 4-09 0.5 glyphosate 4-10 0.5 0.05none 4-11 0.5 0.05 glyphosate 4-12 0.5 0.03 0.02 Silwet L-77 Silwet L-774-13 0.5 0.05 methyl caprate Me caprate 4-14 0.5 0.05 0.05 methylcaprate Me caprate 4-15 0.5 0.05 0.05 methyl caprate Me caprate,glyphosate 4-16 0.5 0.01 PVA none 4-17 0.5 0.01 PVA glyphosate 4-18 0.50.05 0.01 PVA glyphosate 4-19 0.5 0.05 + 0.01 L-77 + PVA Silwet L-77

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and 21 days after planting ECHCF, andevaluation of herbicidal inhibition was done 17 days after application.

In addition to compositions 4-01 to 4-19, spray compositions wereprepared by tank mixing Formulations B and C with Fluorad FC-135 at twoconcentrations. Formulations B and C, alone and tank mixed with 0.5%Silwet 800, were applied as comparative treatments. Results, averagedfor all replicates of each treatment, are shown in Table 4b.

TABLE 4b Glyphosate rate % Inhibition Spray composition g a.e./ha ABUTHECHCF Formulation B 150 13 28 250 37 51 350 56 38 Formulation B + 150 8115 Silwet 800 0.25% v/v 250 89 17 350 91 20 Formulation C 150 32 65 25059 91 350 85 89 Formulation C + 150 91 17 Silwet 800 0.25% v/v 250 91 23350 95 48 Formulation B + 150 31 58 Fluorad FC-135 0.25% w/v 250 53 68350 71 84 Formulation B + 150 31 29 Fluorad FC-135 0.05% w/v 250 44 69350 95 79 Formulation C + 150 46 45 Fluorad FC-135 0.25% w/v 250 69 79350 86 77 Formulation C + 150 44 57 Fluorad FC-135 0.05% w/v 250 60 87350 86 88 4-01 150 55 50 250 87 81 350 89 88 4-02 150 56 54 250 89 69350 87 98 4-03 150 89 68 250 89 84 350 91 90 4-04 150 63 68 250 89 86350 99 89 4-05 150 81 51 250 87 84 350 94 26 4-06 150 67 0 250 93 62 35094 81 4-07 150 81 35 250 84 51 350 95 62 4-08 150 59 51 250 84 69 350 9890 4-09 150 64 59 250 85 61 350 94 96 4-10 150 73 74 250 87 83 350 98 964-11 150 76 64 250 88 79 350 94 81 4-12 150 59 46 250 82 88 350 92 824-13 150 61 45 250 90 69 350 93 90 4-14 150 76 50 250 95 73 350 99 914-15 150 78 67 250 95 80 350 99 85 4-16 150 48 42 250 77 87 350 87 754-17 150 47 63 250 85 67 350 90 78 4-18 150 55 46 250 82 77 350 90 874-19 150 32 23 250 43 31 350 76 65

In this test, addition of methyl caprate to compositions containinglecithin with or without Fluorad FC-135 (4-13 to 4-15) improvedherbicidal effectiveness on ABUTH but had little effect on ECHCF.

Example 5

Aqueous spray compositions were prepared containing glyphosate IPA saltand excipient ingredients as shown in Table 5a. Process (iii) wasfollowed for all compositions, using soybean lecithin (20% phospholipid,Avanti).

TABLE 5a Spray Lecithin % w/w Components composition g/l FC-135 AerosolOT Methyl caprate sonicated with lecithin 5-01 2.5 none 5-02 2.5glyphosate 5-03 1.0 none 5-04 1.0 glyphosate 5-05 0.5 none 5-06 0.5glyphosate 5-07 0.2 none 5-08 0.2 glyphosate 5-09 0.5 0.05 none 5-10 0.50.05 AOT, glyphosate 5-11 0.5 0.05 AOT 5-12 2.5 0.25 none 5-13 0.5 0.05none 5-14 0.5 0.05 glyphosate 5-15 0.5 0.05 Me caprate 5-16 0.5 0.050.05 Me caprate 5-17 0.2 0.02 none 5-18 0.2 0.02 glyphosate 5-19 0.20.02 Me caprate

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF), and prickly sida (Sida spinosa, SIDSP)plants were grown and treated by the standard procedures given above.Applications of spray compositions were made 19 days after plantingABUTH and 22 days after planting ECHCF. No record was found for theplanting date for SIDSP. Evaluation of herbicidal inhibition was done 20days after application.

In addition to compositions 5-01 to 5-19, spray compositions wereprepared by tank mixing Formulations B and C with Fluorad FC-135 atvarious concentrations. Formulations B and C alone were applied ascomparative treatments. Results, averaged for all replicates of eachtreatment, are shown in Table 5b.

TABLE 5b Spray Glyphosate % Inhibition composition rate g a.e./ha ABUTHECHCF SIDSP Formulation B 150 16 23 30 250 17 33 57 350 24 43 65Formulation C 150 18 58 53 250 30 71 79 350 49 83 94 Formulation B + 15027 59 56 Fluorad FC-135 0.25% w/v 250 45 84 81 350 55 82 91 FormulationB + 150 17 43 56 Fluorad FC-135 0.1% w/v 250 21 56 75 350 64 80 90Formulation B + 150 22 27 38 Fluorad FC-135 0.02% w/v 250 37 49 69 35048 68 94 Formulation C + 150 41 41 59 Fluorad FC-135 0.25% w/v 250 57 5385 350 67 67 94 Formulation C + 150 26 39 67 Fluorad FC-135 0.05% w/v250 46 66 88 350 75 73 93 Formulation C + 150 30 52 66 Fluorad FC-1350.02% w/v 250 67 50 89 350 61 88 92 5-01 150 35 62 64 250 63 77 90 35071 83 85 5-02 150 35 44 67 250 53 79 86 350 58 92 90 5-03 150 37 50 71250 53 76 90 350 73 63 97 5-04 150 29 46 61 250 43 77 85 350 70 85 965-05 150 12 36 59 250 43 55 83 350 53 77 87 5-06 150 19 69 67 250 62 4784 350 58 60 95 5-07 150 14 59 59 250 39 63 75 350 46 77 91 5-08 150 3637 64 250 38 68 82 350 47 80 79 5-09 150  8 35 27 250  9 51 56 350 36 5867 5-10 150  5 33 24 250 15 73 47 350 30 66 67 5-11 150 38 49 73 250 6275 89 350 71 75 98 5-12 150  7 41 21 250 18 67 38 350 30 64 61 5-13 15039 72 65 250 65 55 76 350 70 68 90 5-14 150 51 53 66 250 60 82 85 350 6583 95 5-15 150 15 59 61 250 31 54 83 350 57 67 84 5-16 150 36 79 66 25050 60 95 350 71 95 95 5-17 150 30 52 75 250 54 60 84 350 48 84 93 5-18150 43 75 69 250 47 78 88 350 missing missing 90 5-19 150 13 42 61 25029 51 79 350 42 69 90

The inclusion of methyl caprate in a composition containing lecithin andFluorad FC-135 improved efficacy on ECHCF and SIDSP (comparecompositions 5-16 and 5-13).

Example 6

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 6a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi), using Span 80 or Brij 92 (oleth-2) asemulsifier #1 and a Span 80/Tween 80 blend as emulsifier #2.

TABLE 6a % w/w % in inner aq. phase Conc. Glyphosate Orchex Butyl Span80 or Span 80/Tween gly- comp. a.e. 796 stearate Brij 92 80 (45/55)water phosate 6-01 0.4 20.7 0.3 (Span) 10.0 11.5 100 6-02 0.4 20.7 0.3(Span) 10.0 11.5 100 6-03 0.4 20.7 0.3 (Brij) 10.0 11.5 100 6-04 0.420.3 0.8 (Span) 10.0 11.5 100 6-05 0.4 20.3 0.8 (Span) 10.0 11.5 1006-06 0.4 20.3 0.8 (Brij) 10.0 11.5 100 6-07 0.4 19.5 1.5 (Span) 10.011.5 100 6-08 0.4 19.5 1.5 (Span) 10.0 11.5 100 6-09 0.4 19.5 1.5 (Brij)10.0 11.5 100 6-10 0.4 20.0 5.0 (Span) 2.3 35.7 100 6-11 0.4 18.0 3.0(Span) 5.0 11.5 100 6-12 0.8 18.0 3.0 (Span) 5.0 11.5 100 6-13 1.6 18.03.0 (Span) 5.0 11.5 100 6-14 3.2 18.0 3.0 (Span) 5.0 11.5 100 6-15 2.718.0 3.0 (Span) 5.0 11.5 30 6-16 5.3 18.0 3.0 (Span) 5.0 11.5 30 6-1710.7  18.0 3.0 (Span) 5.0 11.5 30 6-18 0.4 18.0 3.0 (Span) 2.3 11.5 100

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 14 days after planting ABUTH and 17 days after planting ECHCF, andevaluation of herbicidal inhibition was done 19 days after application.

Formulations C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 6b.

TABLE 6b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation C 56 5 45 112 20 60 224 79 84 448 97 95Formulation J 56 29 58 112 43 63 224 79 96 448 97 99 6-01 112 48 48 22479 79 448 95 95 6-02 112 65 65 224 93 93 448 96 96 6-03 112 3 3 224 3030 448 71 71 6-04 112 35 35 224 79 79 448 90 90 6-05 112 55 65 224 85 91448 98 95 6-06 112 38 63 224 68 88 448 85 98 6-07 112 30 63 224 60 76448 74 86 6-08 112 45 75 224 95 96 448 99 98 6-09 112 36 70 224 69 71448 97 99 6-10 112 15 55 224 55 78 448 79 90 6-11 112 11 23 224 55 78448 80 95 6-12 112 0 23 224 40 20 448 55 78 6-13 112 1 35 224 15 25 44855 38 6-14 112 0 23 224 0 23 448 25 50 6-15 112 30 40 224 58 75 448 7392 6-16 112 8 43 224 64 55 448 87 84 6-17 112 83 97 224 99 100 448 100100 6-18 112 35 43 224 60 60 448 93 88

Significantly greater herbicidal effectiveness was obtained withcompositions using butyl stearate as the oil (6-02, 6-05, 6-08) thanwith counterparts using Orchex 796 (6-01, 6-04, 6-07).

Example 7

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 7a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi), using Span 80 as emulsifier #1 and a Span80/Tween 80 blend as emulsifier #2.

TABLE 7a % w/w % in inner aq. phase Conc. Glyphosate Orchex Butyl SpanSpan 80/Tween gly- comp. a.e. 796 stearate 80 80 (45/55) water phosate7-01 10.7 18.0 3.0 5.0 12.2 30 7-02 10.7 18.0 3.0 5.0 12.2 20 7-03 10.718.0 3.0 5.0 12.2 0 7-04 10.7 18.0 3.0 5.0 12.2 38 7-05 13.7 18.0 3.05.0 12.2 30 7-06 13.7 18.0 3.0 5.0 12.2 20 7-07 13.7 18.0 3.0 5.0 12.2 07-08 20.5 18.0 3.0 5.0 12.2 20 7-09 20.5 18.0 3.0 5.0 12.2 0 7-10 10.718.0 3.0 5.0 12.2 30 7-11 10.7 18.0 3.0 5.0 12.2 20 7-12 10.7 18.0 3.05.0 12.2 0 7-13 10.7 18.0 3.0 5.0 12.2 38 7-14 13.7 18.0 3.0 5.0 12.2 307-15 13.7 18.0 3.0 5.0 12.2 20 7-16 13.7 18.0 3.0 5.0 12.2 0 7-17 20.518.0 3.0 5.0 12.2 20 7-18 20.5 18.0 3.0 5.0 12.2 0

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 13 days after planting ABUTH and 16 days after planting ECHCF, andevaluation of herbicidal inhibition was done 19 days after application.

Formulations C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 7b.

TABLE 7b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation C  50  1 11 100 35 45 200 46 63 400 97 100 Formulation J  50  5 14 100 33 40 200 70 83 400 93 95 7-01 100 missingmissing 200 missing missing 400 missing missing 7-02 100 missing missing200 missing missing 400 missing missing 7-03 100  5  0 200 58 45 400 7578 7-04 100 missing missing 200 missing missing 400 missing missing 7-05100 missing missing 200 missing missing 400 missing missing 7-06 100  6 5 200 30 35 400 75 73 7-07 100  1  5 200 53 38 400 75 78 7-08 100  8  5200 38 20 400 75 53 7-09 100 11 10 200 59 40 400 78 65 7-10 100 14 28200 36 30 400 74 75 7-11 100  5  5 200 30 40 400 70 55 7-12 100  4  5200  9 25 400 74 46 7-13 100  5  4 200 39 23 400 76 60 7-14 100 10  5200 38 49 400 76 83 7-15 100 11 20 200 51 43 400 80 78 7-16 100 14 20200 50 43 400 86 84 7-17 100 23 25 200 65 53 400 78 79 7-18 100 23 10200 48 40 400 78 81

Many compositions having butyl stearate as the oil showed greaterherbicidal effectiveness than their counterparts having Orchex 796 asthe oil.

Example 8

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient as shown in Table 8a. Process (iv) was followed forall compositions, using soybean lecithin (20% phospholipid, Avanti).

TABLE 8a % w/w Aero- Concentrate Glyphosate Leci- sol MON FC- Methylcomposition g a.e./l thin OT 0818 754 caprate PVA 8-01 200 2.0 0.25 8-02300 3.0 0.50 8-03 300 3.0 0.50 2.0 8-04 200 2.0 0.25 1.5 8-05 200 2.00.25 1.0 1.0 8-06 200 2.0 0.25 1.0 1.0 8-07 200 2.0 0.25 2.0 8-08 2002.0 0.25 8-09 300 3.0 0.50 8-10 300 3.0 0.50 2.0 8-11 200 2.0 0.25 1.58-12 200 2.0 0.25 1.0 8-13 200 2.0 0.25 1.0 8-14 200 2.0 0.25 1.0 1.58-15 200 2.0 0.25 2.0

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and 13 days after planting ECHCF, andevaluation of herbicidal inhibition was done 20 days after application.

Compositions containing PVA were too viscous to spray and were nottested for herbicidal effectiveness. Formulations B, C and J wereapplied as comparative treatments. Results, averaged for all replicatesof each treatment, are shown in Table 8b.

TABLE 8b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 112  5  4 224 48  8 336 73 20 448 94 50Formulation C 112 30 45 224 91 81 336 98 81 448 100  99 Formulation J112 50 35 224 80 65 336 97 88 448 100  90 8-01 112 11  8 224 50 40 33671 61 448 93 78 8-02 112  5  6 224 64 58 336 78 60 448 84 65 8-07 112  5 3 224 46 38 336 73 83 448 93 66 8-08 112  8 13 224 43 46 336 73 65 44883 70 8-09 112  1  5 224 23 25 336 65 33 448 91 58 8-12 112  0  5 224 5848 336 73 63 448 91 63 8-13 112  0 10 224 53 38 336 73 45 448 88 50 8-15112 28 10 224 50 53 336 80 63 448 88 91

Concentrate compositions containing lecithin and methyl caprate did notexhibit herbicidal effectiveness equal to that of the commercialstandards in this test.

Example 9

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 9a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi), using Span 80 as emulsifier #1 and a Span80/Tween 80 blend as emulsifier #2.

TABLE 9a Con- % w/w % in centrate Glypho- Span 80/ inner aq. phase com-sate Butyl Methyl Span Tween 80 glypho- position a.e. stearate oleate 80(45/55) water sate 9-01 6.9 12.0 3.0 5.0 18.8 50 9-02 6.9 12.0 3.0 5.018.8 20 9-03 6.9 12.0 3.0 5.0 18.8  0 9-04 13.8 12.0 3.0 5.0 18.8 209-05 13.8 12.0 3.0 5.0 18.8  0 9-06 30.0 12.0 3.0 5.0 18.8  0 9-07 20.518.0 3.0 5.0 12.2 20 9-08 20.5 18.0 3.0 5.0 12.2  0 9-09 13.8 18.0 3.05.0 12.2 20 9-10 13.8 18.0 3.0 5.0 12.2  0 9-11 6.9 18.0 3.0 5.0 12.2  09-12 30.0 18.0 3.0 5.0 12.2  0 9-13 6.9 18.0 3.0 5.0 12.2 50 9-14 6.918.0 3.0 5.0 12.2 20 9-15 20.5 18.0 3.0 5.0 12.2 20 9-16 13.8 18.0 3.05.0 12.2 20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 15 days after planting ABUTH and 17 days after planting ECHCF, andevaluation of herbicidal inhibition was done 19 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 9b.

TABLE 9b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 224 20 30 336 49 40 448 66 48 Formulation C224 73 80 336 88 98 448 93 99 Formulation J 224 56 69 336 83 85 448 8890 9-01 224 55 35 336 73 66 448 80 78 9-02 224 55 45 336 70 60 448 83 799-03 224 45 40 336 75 76 448 78 83 9-04 224 40 58 336 65 68 448 84 989-05 224 53 55 336 75 85 448 79 88 9-06 224 49 69 336 69 76 448 83 989-07 224 38 45 336 58 63 448 73 75 9-08 224 40 48 336 40 40 448 55 559-09 224 63 53 336 74 78 448 79 83 9-10 224 68 48 336 73 73 448 88 839-11 224 68 46 336 80 80 448 85 97 9-12 224 50 54 336 71 58 448 76 799-13 224 71 65 336 81 87 448 85 89 9-14 224 66 58 336 75 75 448 78 869-15 224 54 49 336 50 65 448 75 75 9-16 224 10 30 336 44 43 448 54 45

Butyl stearate provided herbicidal effectiveness equal or superior tomethyl oleate when used as the oil in compositions of this Example.

Example 10

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 10a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi), using Span 80 as emulsifier #1 and eitherTween 20 or a Span 80/Tween 80 blend as emulsifier #2.

TABLE 10a % w/w % in inner aq. phase Conc. Glyphos- Butyl Span TweenSpan 80/Tween gly- comp. ate a.e. stearate Lecithin 80 20 80 (45/55)water phosate 10-01 10.7 18.0 3.0 5.0 12.2 20 10-02 10.7 18.0 0.6 2.45.0 12.2 20 10-03 10.7 18.0 1.5 1.5 5.0 12.2 20 10-04 10.7 18.0 2.4 0.65.0 12.2 20 10-05 10.7 18.0 3.0 3.0 12.2 20 10-06 10.7 18.0 0.6 2.4 3.012.2 20 10-07 10.7 18.0 1.5 1.5 3.0 12.2 20 10-08 10.7 18.0 2.4 0.6 3.012.2 20 10-09 10.7 7.5 3.0 5.0 5.3 20 10-10 10.7 7.5 0.6 2.4 5.0 5.3 2010-11 10.7 7.5 1.5 1.5 5.0 5.3 20 10-12 10.7 7.5 2.4 0.6 5.0 5.3 2010-13 10.7 7.5 3.0 3.0 5.3 20 10-14 10.7 7.5 0.6 2.4 3.0 5.3 20 10-1510.7 7.5 1.5 1.5 3.0 5.3 20 10-16 10.7 7.5 2.4 0.6 3.0 5.3 20 10-17 10.718.0 3.0 5.0 12.2 20 10-18 10.7 18.0 3.0 5.0 12.2 20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese miller(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and 16 days after planting ECHCF, andevaluation of herbicidal inhibition was done 20 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 10b.

TABLE 10b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 3 10 200 27 20 300 48 40 400 68 43Formulation C 100 20 50 200 50 67 300 73 83 400 82 99 Formulation J 10022 30 200 50 57 300 65 72 400 88 98 10-01 100 17 40 200 55 72 300 67 75400 80 63 10-02 100 12 33 200 53 47 300 72 67 400 77 70 10-03 100 0 15200 0 33 300 15 43 400 40 47 10-04 100 2 12 200 13 27 300 23 33 400 2752 10-05 100 8 43 200 43 40 300 73 53 400 73 90 10-06 100 10 37 200 3375 300 63 63 400 83 87 10-07 100 5 33 200 33 60 300 57 80 400 75 7510-08 100 27 37 200 33 75 300 50 95 400 73 99 10-09 112 5 33 224 47 43336 53 80 448 73 96 10-10 100 0 20 200 10 30 300 47 47 400 47 68 10-11100 0 40 200 17 88 300 47 83 400 73 99 10-12 100 2 50 200 20 63 300 3798 400 67 98 10-13 100 13 43 200 20 90 300 45 89 400 65 99 10-14 100 240 200 33 77 300 47 99 400 60 98 10-15 100 2 57 200 23 77 300 60 90 40060 99 10-16 100 13 68 200 23 91 300 40 77 400 73 97 10-17 100 0 37 20017 78 300 40 86 400 50 85 10-18 100 0 30 200 15 50 300 37 83 400 50 84

Several compositions containing lecithin and butyl stearate outperformedcommercial standard Formulations C and J on ECHCF, but not on ABUTH, inthis test.

Example 11

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 11a. These compositionsare water-in-oil-in-water multiple emulsions and were prepared byprocess (vi) described above, except that method of agitation was variedas indicated below.

TABLE 11a % w/w Conc. Glyphos- Butyl Emuls. Emuls. Emulsifier EmulsifierMethod of comp. ate a.e. stearate #1 #2 #1 #2 agitation (*) 11-01 10.718.0 3.0 5.0 Span 80/lecithin (1:4) Tween 20 11-02 10.7 18.0 3.0 5.0Span 80 Tween 20 11-03 10.7 18.0 3.0 5.0 Span 80 Tween 20 11-04 10.718.0 3.0 5.0 Span 80/lecithin (1:4) Tween 20 11-05 10.7 18.0 3.0 5.0Span 80/lecithin (1:4) Tween 20 11-06 10.0 19.5 1.5 2.5 Pluronic L-81Pluronic L-84 11-07 10.0 19.9 1.3 3.8 Pluronic L-81 Pluronic L-84 11-0810.0 19.9 1.3 3.8 Pluronic L-81 Pluronic L-43 11-09 10.0 19.9 1.3 3.8Pluronic L-81 Pluronic L-84 11-10 10.7 18.0 3.0 5.0 Span 80 Tween 20 A11-11 10.7 18.0 3.0 5.0 Span 80 Tween 20 B 11-12 10.7 18.0 3.0 5.0 Span80 Tween 20 C 11-13 10.7 18.0 3.0 5.0 Span 80 Tween 20 D 11-14 20.5 21.03.0 5.0 Span 80 Span 80/Tween 80 (45/55) B 11-15 13.8 18.0 3.0 5.0 Span80 Span 80/Tween 80 (45/55) A 11-16 20.5 18.0 3.0 5.0 Span 80 Span80/Tween 80 (45/55) A (*) Method of agitation: A Ultrasonic probe BSilverson coarse C Silverson fine D Ultrasonic probe, hand shaking

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 21 days after application.

Formulations B, C and J were applied as comparative treatments. The testwas run twice. Results of the two tests, averaged within tests for allreplicates of each treatment, are shown in Tables 11b and 11c.

TABLE 11b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 1 9 200 9 25 300 27 42 400 44 53Formulation C 100 10 64 200 59 89 300 87 96 400 90 100 Formulation J 1005 28 200 51 72 300 77 92 400 90 99 11-01 100 27 37 200 33 75 300 50 95400 73 99 11-02 100 5 33 200 47 43 300 53 80 400 73 96 11-03 100 13 43200 20 90 300 45 89 400 65 99 11-04 100 2 40 200 33 77 300 47 99 400 6098 11-05 100 2 57 200 23 77 300 60 90 400 60 99 11-06 100 20 10 200 5337 300 68 60 400 87 77 11-07 100 12 20 200 63 30 300 75 63 400 89 7711-08 100 12 20 200 63 30 300 75 63 400 89 77 11-09 112 20 12 224 47 40336 72 90 448 78 78 11-10 100 0 5 200 73 79 300 85 99 400 100 100 11-11100 10 40 200 60 77 300 93 98 400 98 98 11-12 100 67 23 200 76 90 300 9897 400 97 100 11-13 100 7 30 200 75 57 300 92 78 400 98 100 11-14 100 2525 200 78 60 300 90 83 400 98 96 11-15 100 48 58 200 83 96 300 99 100400 100 100 11-16 100 69 35 200 78 76 300 91 97 400 100 99

TABLE 11c Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 0 30 200 8 50 300 55 94 400 71 97Formulation C 100 24 97 200 63 100 300 80 100 400 96 100 Formulation J100 29 100 200 55 99 300 83 100 400 97 100 11-01 100 4 82 200 35 100 30060 99 400 74 100 11-02 100 1 85 200 35 100 300 58 100 400 78 100 11-03100 0 63 200 25 100 300 58 100 400 81 100 11-04 100 1 71 200 15 98 30061 100 400 75 100 11-05 100 30 81 200 35 100 300 50 100 400 76 100 11-06100 0 85 200 55 99 300 78 100 400 85 100 11-07 100 9 90 200 54 99 300 74100 400 89 100 11-08 100 0 83 200 30 100 300 53 100 400 79 100 11-09 1128 94 224 38 97 336 75 100 448 91 100 11-10 100 10 85 200 50 96 300 70100 400 89 100 11-11 100 19 93 200 65 100 300 75 100 400 81 100 11-12100 5 91 200 58 99 300 81 100 400 79 100 11-13 100 8 89 200 65 99 300 76100 400 94 100 11-14 100 13 86 200 33 98 300 70 100 400 83 100 11-15 10020 95 200 66 100 300 73 100 400 89 100 11-16 100 11 93 200 60 100 300 80100 400 78 100

Multiple emulsion compositions of this Example did not outperform thecommercial standards.

Example 12

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 12a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi), using Span 80 as emulsifier #1 and Tween 20 asemulsifier #2. Compositions 12-04, 12-07, 12-09 and 12-11 were madeusing butyl stearate from four different suppliers.

TABLE 12a % w/w % in Gly- inner aq. phase Conc. phosate Span Tween Gly-Type of comp. a.e. Oil 80 20 Water phosate oil 12-01 10 18.0 3.0 5.012.1 20 butyl stearate 12-02 10 7.5 3.0 5.0 5.3 20 butyl stearate 12-0310 7.5 3.0 10.0 5.7 20 butyl stearate 12-04 10 7.5 3.0 10.0 5.7 0 butylstearate 12-05 10 7.5 3.0 10.0 5.7 0 Exxate 700 12-06 10 7.5 3.0 10.05.7 0 Exxate 1000 12-07 10 7.5 3.0 10.0 5.7 0 butyl stearate 12-08 107.5 3.0 10.0 5.7 0 butyl oleate 12-09 10 7.5 3.0 10.0 5.7 0 butylstearate 12-10 10 7.5 3.0 10.0 5.7 0 isopropyl myristate 12-11 10 7.53.0 10.0 5.7 0 butyl stearate 12-12 10 7.5 3.0 10.0 5.7 0 isopropylpalmitate 12-13 10 7.5 3.0 10.0 5.7 0 butyl laurate 12-14 10 7.5 3.010.0 5.7 0 methyl laurate 12-15 10 7.5 3.0 10.0 5.7 0 Exxol D-130 12-1610 7.5 3.0 10.0 5.7 0 Orchex 796 12-17 10 7.5 3.0 10.0 5.7 0 methyloleate 12-18 10 7.5 3.0 10.0 5.7 0 Isopar V 12-19 10 7.5 3.0 10.0 5.7 0soybean oil

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 15 days after planting ABUTH and 15 days after planting ECHCF, andevaluation of herbicidal inhibition was done 21 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 12b.

TABLE 12b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 3 38 200 35 89 300 75 99 400 85 98Formulation J 100 10 35 200 65 84 300 87 100 400 94 100 12-01 100 5 35200 55 75 300 78 85 400 88 98 12-02 100 0 35 200 43 89 300 82 98 400 9599 12-03 100 15 50 200 63 95 300 79 98 400 97 100 12-04 100 4 45 200 6879 300 90 93 400 99 97 12-05 100 1 30 200 40 70 300 70 97 400 89 10012-06 100 3 35 200 38 75 300 70 92 400 84 100 12-07 100 20 53 200 76 96300 84 99 400 95 99 12-08 100 5 25 200 45 81 300 79 94 400 89 99 12-09100 0 35 200 58 96 300 81 100 400 89 100 12-10 100 15 8 200 40 65 300 6884 400 81 99 12-11 100 15 68 200 53 83 300 85 99 400 94 100 12-12 100 1828 200 55 86 300 78 85 400 99 98 12-13 100 6 35 200 48 83 300 69 88 40081 97 12-14 100 13 30 200 50 91 300 78 99 400 84 100 12-15 100 6 23 20035 87 300 73 96 400 86 96 12-16 100 8 38 200 36 45 300 70 99 400 87 9912-17 100 8 75 200 40 96 300 69 98 400 84 98 12-18 100 3 38 200 25 87300 48 94 400 70 91 12-19 100 0 40 200 20 97 300 64 100 400 78 100

Compositions of this Example where the oil was not a fatty acid ester(12-05, 12-06, 12-15, 12-16, 12-18, 12-19) were less herbicidallyeffective than those containing a fatty acid ester.

Example 13

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 13a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi), using Span 80 as emulsifier #1.

TABLE 13a % w/w % in Gly- Butyl Emul- inner aq. phase Conc. phosatestear- Span sifier Gly- Emulsifier comp. a.e. ate 80 #2 Water phosate #213-01 10 18.0 3.0 5.0 12.1 20 Tween 20 13-02 10 7.5 3.0 5.0 5.3 20 Tween20 13-03 10 7.5 3.0 10.0 5.7 0 Tween 20 13-04 10 7.5 3.0 10.0 5.7 0Tween 40 13-05 10 7.5 3.0 10.0 5.7 0 Neodol 25-9 13-06 10 7.5 3.0 10.05.7 0 Neodol 25-12 13-07 10 7.5 3.0 10.0 5.7 0 Tergitol 15-S-20 13-08 107.5 3.0 10.0 5.7 0 Myrj 52 13-09 10 7.5 3.0 10.0 5.7 0 Myrj 59 13-10 107.5 3.0 10.0 5.7 0 Toximul 8240 13-11 15 7.5 3.0 10.0 5.7 0 Tween 2013-12 15 7.5 3.0 10.0 5.7 0 Tween 40 13-13 15 7.5 3.0 10.0 5.7 0 Neodol25-9 13-14 15 7.5 3.0 10.0 5.7 0 Neodol 25-12 13-15 15 7.5 3.0 10.0 5.70 Tergitol 15-S-20 13-16 10 7.5 3.0 10.0 5.7 0 Tween 80 13-17 10 7.5 3.010.0 5.7 0 Tergitol 15-S-15 13-18 10 7.5 3.0 10.0 5.7 0 Neodol 25-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants ere grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and 15 days after planting ECHCF, andevaluation of herbicidal inhibition was done 21 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 13b.

TABLE 13b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 3 28 200 40 50 300 75 83 400 88 93Formulation C 100 5 40 200 51 94 300 80 100 400 95 100 Formulation J 10025 79 200 40 83 300 79 98 400 86 100 13-01 100 20 35 200 53 45 300 95 89400 99 81 13-02 100 9 30 200 35 58 300 79 75 400 86 85 13-03 100 16 30200 56 66 300 83 85 400 88 95 13-04 100 33 40 200 64 64 300 81 91 400 8895 13-05 100 18 33 200 40 79 300 53 90 400 79 96 13-06 100 25 40 200 5376 300 83 93 400 86 100 13-07 100 11 35 200 44 84 300 78 99 400 92 10013-08 100 23 60 200 65 94 300 83 99 400 89 99 13-09 100 25 40 200 30 69300 53 91 400 66 99 13-10 100 5 35 200 43 75 300 65 94 400 76 99 13-11100 10 38 200 48 84 300 78 99 400 81 100 13-12 100 10 45 200 33 89 30070 98 400 83 100 13-13 100 0 35 200 25 68 300 45 93 400 63 96 13-14 10015 45 200 35 92 300 65 100 400 76 99 13-15 100 8 35 200 60 86 300 70 100400 78 100 13-16 100 16 55 200 56 88 300 82 100 400 98 100 13-17 100 3055 200 58 86 300 83 96 400 94 100 13-18 100 33 60 200 71 95 300 86 100400 100 100

Among the most effective compositions in this test were 13-08, 13-16,13-17 and 13-18. The choice of emulsifier #2 had a significant effect onperformance.

Example 14

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 14a. Concentratecompositions 14-01 to 14-17 are water-in-oil-in-water multiple emulsionsand were prepared by process (vi), using Tween 20 as emulsifier #2.Concentrate composition 14-18 is an oil-in-water emulsion and wasprepared by process (vii).

TABLE 14a % w/w Gly- % in phos- Butyl Emul- inner aq. phase Conc. atestear- sifier Tween Gly- Emulsifier comp. a.e. ate #1 20 Water phosate#2 14-01 10 18.0 3.0 5.0 12.0 20 Span 80 14-02 10 7.5 3.0 5.0 5.3 20Span 80 14-03 10 7.5 3.0 10.0 5.7 20 Span 80 14-04 10 7.5 3.0 10.0 5.7 0Span 80 14-05 10 7.5 3.0 10.0 5.7 0 Emid 6545 14-06 10 7.5 3.0 10.0 5.70 Emerest 2421 14-07 10 7.5 3.0 10.0 5.7 0 oleth-2 14-08 10 7.5 3.0 10.05.7 0 Span 65 14-09 10 7.5 3.0 10.0 5.7 0 Span 85 14-10 10 7.5 3.0 10.05.7 0 Span 60 14-11 10 7.5 3.0 10.0 5.7 0 Agrimer AL-30 14-12 10 7.5 3.010.0 5.7 0 Agrimer AL-25 14-13 10 7.5 3.0 10.0 5.7 0 Surfynol 104 14-1410 7.5 3.0 10.0 5.7 0 Neodol 25-3 14-15 10 7.5 3.0 10.0 5.7 0 Neodol91-2.5 14-16 10 7.5 3.0 10.0 5.7 0 Ethomeen C/12 14-17 10 7.5 3.0 10.05.7 0 Ethomeen T/12 14-18 10 7.5 10.0 none

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and 22 days after planting ECHCF, andevaluation of herbicidal inhibition was done 21 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 14b.

TABLE 14b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 18 50 200 18 63 300 53 75 400 43 84Formulation C 100 25 85 200 48 96 300 78 100 400 86 100 Formulation J100 35 92 200 49 99 300 78 99 400 83 99 14-01 100 43 63 200 65 88 300 8593 400 85 100 14-02 100 35 70 200 45 76 300 83 99 400 94 100 14-03 10050 74 200 71 97 300 88 98 400 89 99 14-04 100 64 75 200 75 86 300 93 99400 93 99 14-05 100 65 89 200 79 94 300 93 100 400 94 100 14-06 100 4575 200 75 89 300 85 97 400 83 99 14-07 100 16 45 200 59 83 300 80 90 40090 99 14-08 100 43 84 200 70 97 300 84 93 400 84 100 14-09 100 58 60 20070 89 300 80 97 400 89 99 14-10 100 50 66 200 74 94 300 92 100 400 97100 14-11 100 45 73 200 70 90 300 83 100 400 83 100 14-12 100 missingmissing 200 missing missing 300 missing missing 400 missing missing14-13 100 80 96 200 89 99 300 96 100 400 99 100 14-14 100 35 65 200 7598 300 95 99 400 88 99 14-15 100 51 85 200 55 83 300 83 96 400 81 9814-16 100 55 94 200 65 99 300 83 99 400 84 100 14-17 100 75 99 200 35 97300 92 100 400 81 99 14-18 100 45 90 200 69 75 300 84 100 400 94 100

Most compositions of this Example outperformed commercial standardFormulations C and J on ABUTH. Composition 14-13, using Surfynol 104 asemulsifier #1, was especially efficacious.

Example 15

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 15a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi).

TABLE 15a w/w Conc. Glyphosate Butyl Emulsifier Emulsifier % in inneraq. phase Emulsifier Emulsifier comp. a.e. stearate #1 #2 WaterGlyphosate #1 #2 15-01 10 18.0 3.0 5.0 12.1 20 Span 80 Tween 20 15-02 107.5 3.0 5.0 5.3 20 Span 80 Tween 20 15-03 10 7.5 3.0 10.0 5.7 20 Span 80Tween 20 15-04 10 7.5 3.0 10.0 5.7 0 Span 80 Tween 20 15-05 10 7.5 3.010.0 5.7 0 oleth-2 Neodol 25-12 15-06 10 7.5 3.0 10.0 5.7 0 oleth-2Neodol 25-20 15-07 10 7.5 3.0 10.0 5.7 0 oleth-2 Tween 20 15-08 10 7.53.0 10.0 5.7 0 oleth-2 Tween 40 15-09 10 7.5 3.0 10.0 5.7 0 oleth-2Tween 80 15-10 10 7.5 3.0 10.0 5.7 0 oleth-2 Tergitol 15-S-15 15-11 107.5 3.0 10.0 5.7 0 oleth-2 Tergitol 15-S-20 15-12 10 7.5 3.0 10.0 5.7 0Span 60 Neodol 25-12 15-13 10 7.5 3.0 10.0 5.7 0 Span 60 Neodol 25-2015-14 10 7.5 3.0 10.0 5.7 0 Span 60 Tween 20 15-15 10 7.5 3.0 10.0 5.7 0Span 60 Tween 40 15-16 10 7.5 3.0 10.0 5.7 0 Span 60 Tween 80 15-17 107.5 3.0 10.0 5.7 0 Span 60 Tergitol 15-S-15 15-18 10 7.5 3.0 10.0 5.7 0Span 60 Tergitol 15-S-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and 22 days after planting ECHCF, andevaluation of herbicidal inhibitions was done 20 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 15b.

TABLE 15b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 1 18 200 20 45 300 55 89 400 55 89Formulation C 100 8 85 200 35 89 300 76 95 400 85 98 Formulation J 100 680 200 30 80 300 71 97 400 75 97 15-01 100 35 65 200 65 88 300 78 75 40089 89 15-02 100 14 35 200 40 64 300 83 65 400 58 79 15-03 100 28 38 20073 65 300 73 80 400 91 85 15-04 100 20 55 200 65 60 300 78 87 400 88 9515-05 100 38 45 200 55 65 300 81 84 400 91 83 15-06 100 56 43 200 68 73300 84 80 400 94 80 15-07 100 44 70 200 50 91 300 78 95 400 84 99 15-08100 40 48 200 70 85 300 75 85 400 84 97 15-09 100 53 65 200 73 66 300 8375 400 84 91 15-10 100 20 35 200 60 55 300 76 86 400 84 83 15-11 100 3554 200 70 55 300 83 79 400 95 86 15-12 100 35 55 200 66 74 300 79 84 40095 96 15-13 100 38 60 200 74 66 300 78 91 400 93 90 15-14 100 34 43 20088 69 300 78 92 400 95 92 15-15 100 11 25 200 45 58 300 53 81 400 83 8715-16 100 30 53 200 85 92 300 79 89 400 97 100 15-17 100 28 48 200 66 78300 74 78 400 88 86 15-18 100 18 40 200 63 83 300 76 79 400 81 95

Several compositions of this Example outperformed commercial standardFormulations C and J on ABUTH.

Example 16

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 16a. All concentratecompositions are water-in-oil-in-water multiple emulsions and wereprepared by process (vi).

TABLE 16a % w/w Conc. Glyphosate Butyl Emulsifier Emulsifier % in inneraq. phase Emulsifier Emulsifier comp. a.e. stearate #1 #2 WaterGlyphosate #1 #2 16-01 10 18.0 3.0 5.0 13.8 20 Span 80 Tween 20 16-02 107.5 3.0 5.0 5.6 20 Span 80 Tween 20 16-03 10 6.0 3.0 10.0 8.0 0 Emerest2421 Neodol 25-12 16-04 10 7.5 3.0 10.0 6.0 0 Emerest 2421 Neodol 25-1216-05 10 9.0 3.0 10.0 4.0 0 Emerest 2421 Neodol 25-12 16-06 10 6.0 3.010.0 8.0 0 Emerest 2421 Neodol 25-20 16-07 10 7.5 3.0 10.0 6.0 0 Emerest2421 Neodol 25-20 16-08 10 9.0 3.0 10.0 4.0 0 Emerest 2421 Neodol 25-2016-09 10 6.0 3.0 10.0 8.0 0 Emerest 2421 Tergitol 15-S-15 16-10 10 7.53.0 10.0 6.0 0 Emerest 2421 Tergitol 15-S-15 16-11 10 9.0 3.0 10.0 4.0 0Emerest 2421 Tergitol 15-S-15 16-12 10 6.0 3.0 10.0 8.0 0 Neodol 25-3Neodol 25-12 16-13 10 7.5 3.0 10.0 6.0 0 Neodol 25-3 Neodol 25-12 16-1410 9.0 3.0 10.0 4.0 0 Neodol 25-3 Neodol 25-12 16-15 10 6.0 3.0 10.0 8.00 Neodol 25-3 Neodol 25-20 16-16 10 7.5 3.0 10.0 6.0 0 Neodol 25-3Neodol 25-20 16-17 10 9.0 3.0 10.0 4.0 0 Neodol 25-3 Neodol 25-20 16-1810 6.0 3.0 10.0 8.0 0 Neodol 25-3 Tergitol 15-S-15

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and 18 days after planting ECHCF, andevaluation of herbicidal inhibition was done 19 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 16b.

TABLE 16b Glyphosate rate % Inhibition Concentration composition ga.e./ha ABUTH ECHCF Formulation B 100 30 53 200 76 73 300 78 84 400 8089 Formulation C 100 5 60 200 69 85 300 78 94 400 96 99 Formulation J100 38 55 200 73 91 300 79 98 400 93 100 16-01 100 5 40 200 43 53 300 8669 400 93 79 16-02 100 10 40 200 48 53 300 71 71 400 89 68 16-03 100 1445 200 60 63 300 75 76 400 78 80 16-04 100 50 35 200 69 53 300 79 79 40090 78 16-05 100 35 45 200 76 78 300 80 95 400 95 99 16-06 100 23 55 20070 76 300 80 95 400 94 98 16-07 100 35 66 200 74 93 300 83 95 400 96 9916-08 100 35 40 200 71 83 300 81 97 400 93 99 16-09 100 45 33 200 63 74300 78 85 400 95 85 16-10 100 20 35 200 71 55 300 78 83 400 85 88 16-11100 23 40 200 66 63 300 75 79 400 86 87 16-12 100 20 40 200 66 58 300 7870 400 93 93 16-13 100 20 71 200 69 75 300 78 97 400 86 97 16-14 100 1845 200 73 80 300 83 92 400 90 97 16-15 100 23 45 200 71 78 300 80 98 40091 100 16-16 100 25 73 200 74 81 300 99 91 400 97 100 16-17 100 38 50200 76 83 300 90 85 400 98 89 16-18 100 23 40 200 61 79 300 83 93 400 8890

None of the multiple emulsion compositions of this Example outperformedboth commercial standards in this study.

Example 17

Aqueous concentrate compositions were prepared containing glyphosate IPSsald and excipient ingredients as shown in Table 17a. All arewater-in-oil-in-water multiple emulsions and were prepared by process(vi), using Span 80 as emulsifier #1. Different mixing devices were usedin making the water-in-oil emulsion and the finished multiple emulsionas indicated in the column headed “Process”.

TABLE 17a Conc. Glyphosate Butyl Span Emulsifier Emulsifier % in inneraq. phase Process comp. a.e. stearate 80 #2 #2 Water Glyphosate (*)17-01 10.7 18.0 3.0 5.0 Tween 20 13.8 30 A 17-02 10.7 18.0 3.0 5.0 Tween20 13.8 30 B 17-03 10.7 18.0 3.0 5.0 Tween 20 13.8 30 C 17-04 10.7 18.03.0 5.0 Tween 20 13.8 30 D 17-05 10.7 18.0 3.0 5.0 Tween 20 13.8 30 E17-06 6.9 18.0 3.0 5.0 Span 80/Tween 80 (45/55) 13.8 0 A 17-07 13.8 18.03.0 5.0 Span 80/Tween 80 (45/55) 13.8 0 A 17-08 20.5 18.0 3.0 5.0 Span80/Tween 80 (45/55) 13.8 0 A 17-09 20.5 24.0 3.0 5.0 Span 80/Tween 80(45/55) 4.6 0 C 17-10 10.7 18.0 3.0 5.0 Tween 20 13.8 20 A 17-11 10.018.0 3.0 12.0 Tween 20 15.5 20 A (*) Process: W/O preparation W/O/Wpreparation A Ultrasonic probe Ultrasonic probe B Turrax medium Turraxlow speed speed C Silverson coarse Silverson coarse D Silverson fineSilverson fine E Silverson fine Silverson coarse

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 20 days after planting ABUTH and 22 days after planting ECHCF, andevaluation of herbicidal inhibition was done 20 days after application.Results, averaged for all replicates of each treatment, are shown inTable 17b.

TABLE 17b Glyphosate rate % Inhibition Concentration composition ga.e./ha ABUTH ECHCF Formulation B 100 23 83 200 60 93 300 48 99 400 7597 Formulation C 100 45 94 200 71 93 300 88 99 400 100 100 Formulation J100 10 89 200 73 93 300 78 100 400 96 98 17-01 100 25 68 200 65 86 30080 98 400 97 99 17-02 100 45 84 200 70 90 300 78 100 400 98 100 17-03100 63 79 200 78 95 300 83 100 400 97 100 17-04 100 65 86 200 70 88 30084 96 400 97 100 17-05 100 43 84 200 76 85 300 94 98 400 92 100 17-06100 73 83 200 85 98 300 96 99 400 99 98 17-07 100 48 81 200 78 95 300 9398 400 100 100 17-08 100 60 75 200 74 97 300 88 93 400 97 98 17-09 10051 63 200 68 89 300 79 89 400 91 98 17-10 100 24 53 200 68 89 300 73 83400 95 91 17-11 100 33 58 200 70 94 300 84 82 400 93 93

The choice of mixing device in preparation of multiple emulsioncompositions 17-01 to 17-03 appeared to have some effect on herbicidaleffectiveness in this study.

Example 18

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 18a. Concentratecompositions 18-01 to 18-15 are water-in-oil-in-water multiple emulsionsand were prepared by process (vi). Concentrate compositions 18-16 and18-17 are oil-in-water emulsions and were prepared by process (vii).

TABLE 18a % w/w Conc. Glyphosate Butyl Emulsifier Emulsifier % in inneraq. phase Emulsifier Emulsifier comp. a.e. stearate #1 #2 WaterGlyphosate #1 #2 18-01 10 18.0 3.0 5.0 12.0 20 Span 80 Tween 20 18-02 107.5 3.0 5.0 5.3 20 Span 80 Tween 20 18-03 10 7.5 3.0 10.0 5.7 0 Span 80Tween 20 18-04 10 7.5 3.0 10.0 5.7 0 Emerest 2421 Neodol 25-12 18-05 107.5 3.0 10.0 5.7 0 Emerest 2421 Neodol 25-20 18-06 10 7.5 3.0 10.0 5.7 0Emerest 2421 Tergitol 15-S-15 18-07 10 7.5 3.0 10.0 5.7 0 Emid 6545Neodol 25-12 18-08 10 7.5 3.0 10.0 5.7 0 Emid 6545 Neodol 25-20 18-09 107.5 3.0 10.0 5.7 0 Emid 6545 Tergitol 15-S-15 18-10 10 7.5 3.0 10.0 5.70 Neodol 25-3 Neodol 25-12 18-11 10 7.5 3.0 10.0 5.7 0 Neodol 25-3Neodol 25-20 18-12 10 7.5 3.0 10.0 5.7 0 Neodol 25-3 Tergitol 15-S-1518-13 10 7.5 3.0 10.0 5.7 0 Span 80 Neodol 25-12 18-14 10 7.5 3.0 10.05.7 0 Span 80 Neodol 25-20 18-15 10 7.5 3.0 10.0 5.7 0 Span 80 Tergitol15-S-15 18-16 10 7.5 10.0 none Neodol 25-12 18-17 10 7.5 10.0 noneNeodol 25-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and 18 days after planting ECHCF, andevaluation of herbicidal inhibition was done 17 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 18b.

TABLE 18b Glyphosate rate % Inhibition Concentration composition ga.e./ha ABUTH ECHCF Formulation B 150 0 28 250 20 41 350 41 72 450 70 85Formulation C 150 55 83 250 88 100 350 99 100 450 100 100 Formulation J150 43 63 250 88 100 350 94 100 450 99 100 18-01 150 82 81 250 76 90 35098 95 450 100 100 18-02 150 23 59 250 67 92 350 91 100 450 97 98 18-03150 40 59 250 85 99 350 94 99 450 100 100 18-04 150 41 55 250 83 97 35090 99 450 94 99 18-05 150 49 80 250 84 85 350 94 99 450 99 100 18-06 15038 57 250 78 93 350 94 99 450 98 97 18-07 150 57 69 250 83 95 350 95 99450 100 96 18-08 150 52 67 250 83 96 350 93 100 450 99 100 18-09 150 4571 250 80 89 350 89 97 450 97 100 18-10 150 59 65 250 87 89 350 95 98450 97 94 18-11 150 73 74 250 91 91 350 98 99 450 100 100 18-12 150 5771 250 85 89 350 95 99 450 100 99 18-13 150 45 72 250 87 87 350 90 95450 96 100 18-14 150 45 85 250 89 99 350 96 99 450 98 100 18-15 150 4083 250 83 98 350 93 99 450 96 100 18-16 150 65 79 250 87 99 350 96 99450 100 100 18-17 150 59 80 250 95 86 350 100 99 450 100 100

Simple emulsion compositions of this example containing butyl stearate(18-16 and 18-17) exhibited herbicidal effectiveness at least equal tomultiple emulsion compositions having the same emulsifier #2.

Example 19

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 19a. These compositionsare water-in-oil-in-water multiple emulsions and were prepared byprocess (vi) described above.

TABLE 19a % w/w Conc. Glyphos- Butyl Emulsifier Emulsifier % in inneraq. phase Emulsifier Emulsifier comp. ate a.e. stearate #1 #2 WaterGlyphosate #1 #2 19-01 10 18.0 3.0 5.0 9.0 20 Span 80 Tween 20 19-02 107.5 3.0 5.0 4.5 20 Span 80 Tween 20 19-03 10 7.5 3.0 10.0 4.5 0 Surfynol104 Neodol 25-12 19-04 10 7.5 3.0 10.0 4.5 0 Surfynol 104 Neodol 25-2019-05 10 7.5 3.0 10.0 4.5 0 Surfynol 104 Tergitol 15-S-15 19-06 10 7.53.0 10.0 4.5 0 Surfynol 104 Tergitol 15-S-20 19-07 10 7.5 3.0 10.0 4.5 0Surfynol 104 Tween 20 19-08 10 7.5 3.0 10.0 4.5 0 Surfynol 104ceteareth-55 19-09 10 7.5 3.0 10.0 4.5 0 Surfynol 104 Tergitol 15-S-3019-10 10 7.5 3.0 10.0 4.5 0 Neodol 25-3 ceteareth-55 19-11 10 7.5 3.010.0 4.5 0 Neodol 25-3 Tergitol 15-S-30 19-12 10 7.5 3.0 10.0 4.5 0 Span60 ceteareth-55 19-13 10 7.5 3.0 10.0 4.5 0 Span 60 Tergitol 15-S-3019-14 10 7.5 3.0 10.0 4.5 0 oleth-2 ceteareth-55 19-15 10 7.5 3.0 10.04.5 0 oleth-2 Tergitol 15-S-30 19-16 10 7.5 3.0 10.0 4.5 0 Emid 6545ceteareth-55 19-17 10 7.5 3.0 10.0 4.5 0 Emid 6545 Tergitol 15-S-30

Velvet leaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Application of spray compositions weremade 35 days after planting ABUTH and 33 days after planting ECHCF, andevaluation of herbicidal inhibition was done 17 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 19b.

TABLE 19b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 0 250 35 40 350 50 63 450 60 43Formulation C 150 63 63 250 80 96 350 92 98 450 98 87 Formulation J 15043 30 250 75 85 350 82 98 450 96 95 19-01 150 65 53 250 85 70 350 90 87450 98 73 19-02 150 63 5 250 78 53 350 88 80 450 97 87 19-03 150 75 0250 87 22 350 88 72 450 97 17 19-04 150 84 0 250 90 10 350 95 70 450 9860 19-05 150 77 0 250 83 3 350 93 30 450 95 10 19-06 150 72 0 250 83 47350 94 60 450 98 20 19-07 150 75 0 250 77 40 350 96 47 450 96 50 19-08150 87 40 250 97 82 350 99 83 450 100 77 19-09 150 82 10 250 82 40 35096 67 450 97 67 19-10 150 82 13 250 94 83 350 99 85 450 99 83 19-11 15073 17 250 83 60 350 88 73 450 96 63 19-12 150 80 20 250 93 85 350 96 82450 96 82 19-13 150 78 20 250 83 50 350 92 90 450 92 85 19-14 150 80 30250 97 85 350 99 99 450 97 96 19-15 150 82 30 250 87 75 350 99 92 450 9993 19-16 150 82 53 250 96 82 350 96 97 450 87 82 19-17 150 72 20 250 8063 350 92 75 450 95 87

Considerable variation was seen in herbicidal effectiveness ofwater-in-oil-in-water multiple emulsions of this Example, especially onECHCF. Among the most efficacious were 19-08, 19-10, 19-12, 19-14, and19-16. All of these contained a C₁₆₋₁₈ alkylether surfactant,ceteareth-55. When Tergitol 15-S-30, a C₁₂₋₁₅ secondary alkylethersurfactant, replaced ceteareth-55, as in 19-09, 19-11, 19-13, 19-15 and19-17, herbicidal effectiveness, at least on ECHCF, was in most casesmarkedly reduced.

Example 20

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 20a. Concentratecompositions 20-01 and 20-02 are water-in-oil-in-water multipleemulsions and were prepared by process (vi), using Span 80 as emulsifier#1. Concentrate compositions 20-03 to 20-12 and 20-14 to 20-17 areoil-in-water emulsions and were prepared by process (vii). Concentratecomposition 20-13 is an aqueous solution concentrate and was prepared byprocess (viii), the component indicated below as “emulsifier #2” beingthe surfactant component.

TABLE 20a % w/w % in Gly- Butyl Emul- inner aq. phase Conc. phosatestear- Span sifier Gly- Emulsifier comp. a.e. ate 80 #2 Water phosate #220-01 10 18.0 3.0 5.0 12.2 20 Tween 20 20-02 10 7.5 3.0 5.0 5.3 20 Tween20 20-03 10 1.0 10.0 Neodol 25-20 20-04 10 3.0 10.0 Neodol 25-20 20-0510 1.0 5.0 Neodol 25-20 20-06 10 3.0 5.0 Neodol 25-20 20-07 15 1.0 10.0Neodol 25-20 20-08 15 3.0 10.0 Neodol 25-20 20-09 15 1.0 5.0 Neodol25-20 20-10 15 3.0 5.0 Neodol 25-20 20-11 20 1.0 5.0 Neodol 25-20 20-1220 1.0 10.0 Neodol 25-20 20-13 10 10.0 Neodol 25-20 20-14 10 7.5 10.0Neodol 25-20 20-15 10 7.5 10.0 Neodol 25-12 20-16 10 7.5 10.0 steareth-20 20-17 10 7.5 10.0 oleth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and 19 days after planting ECHCF, andevaluation of herbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 20b.

TABLE 20b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 30 250 10 40 350 37 73 450 58 68Formulation C 150 42 79 250 77 98 350 99 97 450 97 93 Formulation J 15043 67 250 73 90 350 94 98 450 77 78 20-01 150 58 76 250 75 77 350 88 93450 95 83 20-02 150 27 63 250 60 87 350 82 98 450 77 92 20-03 150 47 76250 65 92 350 94 99 450 95 91 20-04 150 70 86 250 86 95 350 97 98 450 9990 20-05 150 42 80 250 72 90 350 90 93 450 99 96 20-06 150 48 57 250 7892 350 94 99 450 96 92 20-07 150 78 95 250 96 96 350 98 98 450 100 9720-08 150 88 96 250 98 98 350 100 99 450 100 99 20-09 150 82 93 250 9496 350 99 97 450 99 93 20-10 150 72 83 250 97 93 350 99 100 450 100 9820-11 150 87 83 250 98 97 350 100 99 450 100 99 20-12 150 93 99 250 9999 350 99 97 450 100 99 20-13 150 70 90 250 91 88 350 97 94 450 99 8620-14 150 67 76 250 93 80 350 98 95 450 95 78 20-15 150 68 65 250 90 87350 97 80 450 98 93 20-16 150 83 73 250 90 93 350 99 100 450 100 10020-17 150 80 66 250 98 77 350 99 83 450 100 85

Very high herbicidal activity was evident in compositions 20-13 to20-17, which have a very high ratio of surfactant to glyphosate a.e. of1:1. Activity was too high to clearly distinguish among thesecompositions, but 20-16 and 20-17, containing steareth-20 and oleth-20respectively, exhibited greater effectiveness on ABUTH at the lowestglyphosate rate than 20-14 and 20-15, containing Neodol 25-20 and Neodol25-12 respectively.

Example 21

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 21a. Concentratecompositions 21-01 and 21-02 are water-in-oil-in-water multipleemulsions and were prepared by process (vi), using Span 80 as emulsifier#1. Concentrate compositions 21-03 to 21-12 and 21-14 to 21-17 areoil-in-water emulsions and were prepared by process (vii). Concentratecomposition 21-13 is an aqueous solution concentrate and was prepared byprocess (viii), the component indicated below as “emulsifier #2” beingthe surfactant component.

TABLE 21a % w/w Conc. Glyphosate Butyl Emulsifier % in inner aq. phaseEmulsifier comp. a.e. stearate Span 80 #2 Water Glyphosate #2 21-01 1018.0 3.0 5.0 12.2 20 Tween 20 21-02 10 7.5 3.0 5.0 5.3 20 Tween 20 21-0310 1.0 10.0 Tween 80 21-04 10 3.0 10.0 Tween 80 21-05 10 1.0 5.0 Tween80 21-06 10 3.0 5.0 Tween 80 21-07 15 1.0 10.0 Tween 80 21-08 15 3.010.0 Tween 80 21-09 15 1.0 5.0 Tween 80 21-10 15 3.0 5.0 Tween 80 21-1120 1.0 5.0 Tween 80 21-12 20 1.0 10.0 Tween 80 21-13 10 10.0 Tween 8021-14 10 7.5 10.0 Tween 80 21-15 10 7.5 10.0 Neodol 25-20 21-16 10 7.510.0 steareth-20 21-17 10 7.5 10.0 oleth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and 19 days after planting ECHCF, andevaluation of herbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 21b.

TABLE 21b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 0 250 3 10 350 17 20 450 20 30Formulation C 150 70 33 250 80 70 350 85 80 450 97 77 Formulation J 1507 20 250 70 80 350 78 80 450 83 80 21-01 150 40 7 250 48 20 350 73 23450 75 30 21-02 150 3 0 250 10 17 350 47 23 450 50 30 21-03 150 0 2 25033 13 350 63 40 450 68 43 21-04 150 17 7 250 43 20 350 78 63 450 78 6321-05 150 10 3 250 20 13 350 58 40 450 75 40 21-06 150 3 0 250 27 20 35060 23 450 72 23 21-07 150 32 10 250 68 20 350 75 50 450 86 60 21-08 15027 20 250 68 30 350 82 40 450 90 73 21-09 150 43 10 250 60 33 350 72 63450 75 73 21-10 150 33 10 250 62 30 350 77 60 450 83 70 21-11 150 48 13250 72 63 350 83 80 450 87 80 21-12 150 23 13 250 60 50 350 75 80 450 8678 21-13 150 32 13 250 47 40 350 75 50 450 78 70 21-14 150 27 20 250 7553 350 82 70 450 92 67 21-15 150 70 20 250 78 30 350 92 80 450 93 8021-16 150 68 40 250 73 30 350 93 80 450 93 77 21-17 150 73 20 250 85 30350 93 60 450 95 63

Compositions 21-16 and 21-17, containing steareth-20 and oleth-20respectively, exhibited very high herbicidal activity on ABUTH. At thevery high surfactant to glyphosate a.e. ratio (1:1) of thesecompositions, no difference was evident between these compositions andan otherwise similar compositions (21-15) containing Neodol 25-20 inplace of steareth-20 or oleth-20.

Example 22

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 22a. Concentratecompositions 22-01 and 22-02 are water-in-oil-in-water multipleemulsions and were prepared by process (vi), using Span 80 as emulsifier#1. Concentrate compositions 22-03 to 22-16 are oil-in-water emulsionsand were prepared by process (vii).

TABLE 22a % w/w Concentrate Glyphosate Butyl Span Emulsifier Aerosil %in inner aq. phase Emulsifier composition a.e. stearate 80 #2 90 WaterGlyphosate #2 22-01 10 18.0 3.0 5.0 12.2 20 Tween 20 22-02 10 7.5 3.05.0 5.3 20 Tween 20 22-03 10 7.5 10.0 Tween 80 22-04 15 7.5 10.0 Tween80 22-05 15 7.5 1.0 0.40 Tween 80 22-06 15 7.5 0.40 22-07 15 7.5 5.00.40 Tween 80 22-08 15 7.5 10.0 0.25 Tween 80 22-09 30 15.0 10.0 0.80Tween 80 22-10 15 3.0 10.0 Tween 80 22-11 15 1.0 10.0 Tween 80 22-12 307.5 10.0 Tween 80 22-13 30 3.0 10.0 Tween 80 22-14 30 1.0 10.0 Tween 8022-15 30 7.5 10.0 0.80 Tween 80 22-16 30 3.0 10.0 0.80 Tween 80

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Apllications of spray compositions weremade 17 days after planting ABUTH and 19 days after planting ECHCF, andevaluation of herbicidal inhibition was done 17 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 22b.

TABLE 22b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 7 250 3 10 350 35 25 450 60 27Formulation C 150 37 25 250 65 60 350 80 78 450 86 88 Formulation J 15023 25 250 70 63 350 83 60 450 92 73 22-01 150 55 22 250 65 25 350 72 30450 78 53 22-02 150 45 15 250 62 20 350 77 27 450 78 30 22-03 150 48 23250 65 25 350 77 30 450 83 62 22-04 150 50 25 250 65 28 350 73 47 450 8083 22-05 150 18 10 250 57 25 350 63 25 450 68 55 22-06 150 0 10 250 4825 350 60 25 450 63 27 22-07 150 50 25 250 62 27 350 78 33 450 84 3322-08 150 47 25 250 60 28 350 75 55 450 85 30 22-09 150 43 18 250 67 20350 78 25 450 80 28 22-10 150 48 30 250 60 33 350 78 30 450 82 33 22-11150 43 22 250 60 38 350 65 33 450 80 32 22-12 150 43 25 250 60 25 350 7330 450 78 30 22-13 150 53 30 250 63 40 350 67 30 450 82 30 22-14 150 1020 250 57 25 350 73 27 450 78 30 22-15 150 30 20 250 60 25 350 65 25 45073 28 22-16 150 17 10 250 55 25 350 73 40 450 78 30

None of the emulsion compositions of this Example gave herbicidaleffectiveness greater than obtained with the commercial standards.

Example 23

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 23a. Concentratecompositions 23-01 and 23-02 are water-in-oil-in-water multipleemulsions and were prepared by process (vi), using Span 80 as emulsifier#1. Concentrate compositions 23-03 to 23-17 are oil-in-water emulsionsand were prepared by process (vii).

TABLE 23a % w/w Concentrate Glyphosate Butyl Span Emulsifier Aerosil %in inner aq. phase Emulsifier composition a.e. stearate 80 #2 90 WaterGlyphosate #2 23-01 10 18.0 3.0 5.0 12.2 20 Tween 20 23-02 10 7.5 3.05.0 5.3 20 Tween 20 23-03 10 7.5 10.0 Neodol 25-20 23-04 15 7.5 10.0Neodol 25-20 23-05 15 7.5 1.0 0.40 Neodol 25-20 23-06 15 7.5 0.40 Neodol25-20 23-07 15 7.5 5.0 0.40 Neodol 25-20 23-08 15 7.5 10.0 0.25 Neodol25-20 23-09 30 15.0 10.0 0.80 Neodol 25-20 23-10 15 3.0 10.0 Neodol25-20 23-11 15 1.0 10.0 Neodol 25-20 23-12 15 7.5 5.0 Neodol 25-12 23-1315 3.0 5.0 Neodol 25-12 23-14 10 3.0 5.0 Neodol 25-12 23-15 10 3.0 10.0Neodol 25-12 23-16 10 7.5 10.0 Neodol 25-12 23-17 10 7.5 5.0 Neodol25-12

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 20 days after planting ABUTH and 22 days after planting ECHCF, andevaluation of herbicidal inhibition was done 15 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 23b.

TABLE 23b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 13 5 250 48 33 350 57 40 450 77 47Formulation C 150 65 63 250 83 80 350 96 95 450 96 96 Formulation J 15050 57 250 83 86 350 88 90 450 95 93 23-01 150 43 63 250 73 99 350 78 72450 90 88 23-02 150 33 30 250 70 73 350 82 53 450 83 94 23-03 150 60 60250 78 98 350 94 97 450 92 98 23-04 150 53 57 250 83 69 350 93 90 450 9063 23-05 150 25 43 250 65 53 350 73 70 450 82 98 23-06 150 15 33 250 4770 350 70 60 450 77 67 23-07 150 47 47 250 75 70 350 80 78 450 88 9023-08 150 53 43 250 75 57 350 92 79 450 93 93 23-09 150 32 40 250 68 57350 82 88 450 85 98 23-10 150 47 67 250 78 78 350 92 88 450 98 96 23-11150 43 40 250 72 82 350 83 97 450 87 97 23-12 150 70 77 250 88 85 350 9595 450 98 96 23-13 150 63 67 250 83 97 350 96 98 450 97 97 23-14 150 5770 250 83 85 350 88 98 450 97 92 23-15 150 63 70 250 75 88 350 93 95 45097 99 23-16 150 70 50 250 83 70 350 87 91 450 96 96 23-17 150 43 37 25077 70 350 90 85 450 93 89

The overall level of herbicidal effectiveness in this study wasextremely high, making it difficult to determine if any of the emulsioncompositions showed enhancement over the commercial standards.

Example 24

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 24a. All concentratecompositions are oil-in-water emulsions and were prepared by process(vii).

TABLE 24a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 24-01 163 1.00 10.0 Tween 80 24-02163 1.00 10.0 Neodol 25-12 24-03 163 1.00 10.0 Neodol 25-20 24-04 1631.00 10.0 steareth-20 24-05 163 1.00 10.0 oleth-20 24-06 163 1.00 10.0Tergitol 15-S-40 24-07 163 1.00 10.0 Tergitol 15-S-15 24-08 163 1.0010.0 Tergitol 15-S-20 24-09 163 0.50 10.0 Tergitol 15-S-40 24-10 1630.50 10.0 Tergitol 15-S-15 24-11 163 0.50 10.0 Tergitol 15-S-20 24-12163 0.50 5.0 Tergitol 15-S-40 24-13 163 0.50 5.0 Tergitol 15-S-15 24-14163 0.50 5.0 Tergitol 15-S-20 24-15 163 0.25 10.0 Tergitol 15-S-40

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 19 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 24b.

TABLE 24b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 2 20 250 2 30 350 5 53 450 45 75Formulation C 150 45 63 250 77 93 350 83 99 450 93 100  Formulation J150 15 40 250 70 73 350 78 98 450 92 99 24-01 150 42 50 250 72 89 350 8096 450 93 98 24-02 150 45 80 250 72 83 350 85 91 450 97 98 24-03 150 6080 250 75 87 350 82 96 450 86 99 24-04 150 65 60 250 82 70 350 93 80 45098 87 24-05 150 72 60 250 83 87 350 95 93 450 98 97 24-06 150 50 45 25068 70 350 77 85 450 83 90 24-07 150 25 40 250 65 50 350 80 77 450 83 8024-08 150 37 33 250 72 80 350 77 87 450 80 90 24-09 150 32 47 250 65 73350 77 75 450 80 94 24-10 150 17 30 250 65 70 350 75 70 450 78 89 24-11150 35 33 250 68 68 350 77 77 450 92 75 24-12 150 13 35 250 57 40 350 7557 450 77 83 24-13 150 35 40 250 63 43 350 77 77 450 83 75 24-14 150 3025 250 67 53 350 78 85 450 83 77 24-15 150 13 37 250 65 50 350 77 57 45087 82

At a surfactant to glyphosate a.e. weight/weight ratio of about 1:1.5,compositions containing steareth-20 or oleth-20 (24-04 and 24-05respectively) exhibited herbicidal effectiveness on ABUTH similar to onecontaining Neodol 25-20 (24-03).

Example 25

Glyphosate-containing spray compositions were prepared by tank-mixingFormulations B and C with butyl stearate as shown in Table 25.

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 17 days after application.

Results, averaged for all replicates of each treatment, are shown inTable 25.

TABLE 25 Glyphosate Additive Glyphosate rate rate % Inhibitioncomposition g a.e./ha Additive % v/v ABUTH ECHCF Formulation 200 none 1030 B 300 30 40 400 63 57 Formulation 200 MON 0.09 68 70 B 300 0818 80 85400 97 93 Formulation 200 butyl 0.005 75 86 B 300 stearate 80 96 400 8397 Formulation 200 butyl 0.01 73 82 B 300 stearate 77 88 400 88 86Formulation 200 butyl 0.05 65 82 B 300 stearate 78 82 400 94 96Formulation 200 butyl 0.1 75 68 B 300 stearate 80 82 400 94 94Formulation 200 butyl 0.2 75 70 B 300 stearate 83 73 400 95 96Formulation 200 butyl 0.5 80 73 B 300 stearate 96 82 400 96 83Formulation 200 butyl 1.0 90 82 B 300 stearate 93 85 400 97 87

Surprisingly the addition of extremely low concentrations of butylstearate to Formulation B greatly enhanced herbicidal effectiveness inthis study.

Example 26

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 26a. Process (v) wasfollowed for all compositions using soybean lecithin (45% phospholipid,Avanti).

TABLE 26a Concen- % w/w trate Gly- com- phosate Leci- Butyl Fluorad MONEthomeen position a.e. thin stearate FC-754 0818 T/25 Ethanol 26-01 202.0 0.5 1.25 1.0 26-02 20 2.0 0.5 1.00 1.00 1.0 26-03 20 2.0 0.5 1.251.0 26-04 20 6.0 1.5 3.00 3.0 26-05 20 6.0 1.5 2.00 2.00 2.0 26-06 206.0 1.5 3.00 3.0 26-07 20 2.0 0.5 0.50 26-08 20 2.0 0.5 2.50 26-09 202.0 0.5 1.25 1.25 26-10 20 6.0 1.5 0.50 26-11 20 6.0 1.5 3.00 26-12 206.0 1.5 6.00 26-13 20 6.0 1.5 3.00 3.00 26-14 20 2.0 2.0 0.50 26-15 206.0 3.0 6.00 26-16 20 6.0 6.0 6.00

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 15 days after application.

Formulation J was applied as a comparative treatment. Results, averagedfor all replicates of each treatment, are shown in Table 26b.

TABLE 26b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation J 150 38 45 250 80 63 350 78 82 450 75 55 26-01150 23 27 250 57 53 350 70 85 450 70 83 26-02 150 7 25 250 52 45 350 8288 450 82 90 26-03 150 38 35 250 50 40 350 82 92 450 83 93 26-04 150 4048 250 73 75 350 78 92 450 88 92 26-05 150 50 53 250 68 80 350 85 98 45089 96 26-06 150 50 43 250 55 80 350 78 97 450 85 91 26-07 150 3 28 25022 43 350 67 72 450 73 75 26-08 150 43 33 250 77 63 350 89 78 450 97 8526-09 150 57 27 250 95 63 350 89 86 450 98 88 26-10 150 32 23 250 33 55350 73 82 450 67 60 26-11 150 45 32 250 78 72 350 95 92 450 98 96 26-12150 67 42 250 80 75 350 96 88 450 97 90 26-13 150 73 42 250 83 77 350 9691 450 98 88 26-14 150 57 30 250 77 72 350 84 80 450 96 75 26-15 150 7238 250 88 82 350 98 92 450 98 87 26-16 150 85 49 250 97 47 350 97 83 45098 85

Performing very well in this test, particularly on ECHCF, were a numberof concentrate compositions containing lecithin and butyl stearate.

Example 27

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 27a. All areoil-in-water emulsions and were prepared by process (vii).

TABLE 27a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 27-01 163 1.0 10.0 Tween 80 27-02163 1.0 10.0 Neodol 25-12 27-03 163 1.0 10.0 Neodol 25-20 27-04 163 1.010.0 steareth-20 27-05 163 1.0 10.0 oleth-20 27-06 163 1.0 10.0 Tergitol15-S-40 27-07 163 1.0 10.0 Tergitol 15-S-15 27-08 163 1.0 10.0 Tergitol15-S-20 27-09 163 0.5 10.0 Tergitol 15-S-40 27-10 163 0.3 10.0 Tergitol15-S-15 27-11 163 0.3 10.0 Tergitol 15-S-20 27-12 163 0.3 10.0 Tergitol15-S-40 27-13 163 0.3 5.0 Tergitol 15-S-15 27-14 163 0.3 5.0 Tergitol15-S-20 27-15 163 0.3 5.0 Tergitol 15-S-40

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 21 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 27b.

TABLE 27b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 23 250 0 40 350 5 53 450 13 57Formulation C 150 0 47 250 28 87 350 72 98 450 97 97 Formulation J 150 540 250 20 63 350 67 93 450 82 92 27-01 150 2 40 250 30 50 350 50 70 45057 85 27-02 150 10 50 250 33 50 350 75 72 450 75 88 27-03 150 17 53 25060 60 350 70 92 450 78 94 27-04 150 57 45 250 70 70 350 82 93 450 83 9527-05 150 47 45 250 70 80 350 80 88 450 88 92 27-06 150 2 42 250 20 60350 35 75 450 58 89 27-07 150 0 42 250 30 68 350 40 75 450 77 82 27-08150 2 40 250 25 60 350 50 83 450 75 86 27-09 150 2 43 250 27 83 350 4073 450 70 78 27-10 150 2 42 250 32 47 350 43 63 450 70 82 27-11 150 0 30250 25 53 350 35 75 450 70 75 27-12 150 2 40 250 13 57 350 25 75 450 4083 27-13 150 5 42 250 23 62 350 38 63 450 67 60 27-14 150 2 33 250 13 48350 30 53 450 70 88 27-15 150 2 33 250 18 48 350 30 75 450 43 65

In this test, at a surfactant to glyphosate a.e. weight/weight ratio ofabout 1:1.5, compositions containing steareth-20 or oleth-20 (27-04 and27-05 respectively) exhibited greater herbicidal effectiveness on bothABUTH and ECHCF than one containing Neodol 25-20 (27-03).

Example 28

Aqueous concentrate compositions were prepared containing glyphosateammonium or IPA salt excipient ingredients as shown in Table 28a.Concentrate composition 28-01 is a water-in-oil-in-water multipleemulsion and was prepared by process (vi), using Span 80 as emulsifier#1. Concentrate compositions 28-02 to 28-11 and 28-17 are oil-in-wateremulsions and were prepared by process (vii). Concentrate compositions28-12 to 28-16 are aqueous solution concentrates and were prepared byprocess (viii), the component indicated below as “emulsifier #2” beingthe surfactant component.

TABLE 28a % w/w Conc. Glyphos- Butyl Span Emulsifier % in inner aq.phase Emulsifier Glyphosate comp. ate a.e. stearate 80 #2 WaterGlyphosate #2 salt 28-01 10 18.0  3.0  5.0 9.0 20 Tween 20 IPA 28-02 151.0 10.0 Tween 80 IPA 28-03 15 1.0 10.0 Neodol 25-12 IPA 28-04 15 1.010.0 Neodol 25-20 IPA 28-05 15 1.0 10.0 steareth-20 IPA 28-06 15 1.010.0 oleth-20 IPA 28-07 15 1.0 10.0 Tween 80 ammonium 28-08 15 1.0 10.0Neodol 25-12 ammonium 28-09 15 1.0 10.0 Neodol 25-20 ammonium 28-10 151.0 10.0 steareth-20 ammonium 28-11 15 1.0 10.0 oleth-20 ammonium 28-1215 10.0 Tween 80 IPA 28-13 15 10.0 Neodol 25-12 IPA 28-14 15 10.0 Neodol25-20 IPA 28-15 15 10.0 steareth-20 IPA 28-16 15 10.0 oleth-20 IPA 28-1715 1.0 10.0 Emerest 2661 IPA

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 20 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 28b.

TABLE 28b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 2 5 250 3 25 350 28 30 450 53 50Formulation C 150 5 25 250 60 50 350 85 83 450 88 88 Formulation J 150 210 250 70 40 350 82 53 450 87 83 28-01 150 23 20 250 72 30 350 80 80 45085 69 28-02 150 5 18 250 72 38 350 82 63 450 85 83 28-03 150 25 20 25070 57 350 85 68 450 90 83 28-04 150 25 27 250 77 67 350 85 62 450 88 7028-05 150 60 25 250 82 62 350 87 73 450 85 80 28-06 150 50 32 250 78 78350 91 91 450 98 98 28-07 150 5 25 250 55 77 350 77 86 450 83 99 28-08150 0 13 250 58 78 350 80 85 450 85 87 28-09 150 7 25 250 57 72 350 7783 450 91 92 28-10 150 50 25 250 80 55 350 86 87 450 92 82 28-11 150 5330 250 78 80 350 87 89 450 95 98 28-12 150 0 25 250 50 77 350 77 90 45083 94 28-13 150 2 30 250 55 75 350 72 92 450 85 80 28-14 150 12 30 25075 78 350 84 90 450 96 94 28-15 150 55 35 250 78 80 350 80 94 450 86 9828-16 150 50 35 250 73 63 350 84 83 450 89 95 28-17 150 0 10 250 10 53350 53 83 450 62 87

Compositions containing steareth-20 or oleth (28-05, 28-06, 28-10,28-11, 28-15, 28-16) generally exhibited superior herbicidaleffectiveness to counterparts containing Neodol 25-20 (28-04, 28-09,28-14), at least on ABUTH. The presence of a small amount of butylstearate tended to enhance effectiveness on ABUTH (compare 28-05 and28-06 with 28-15 and 28-16).

Example 29

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 29a. Concentratecomposition 29-01 is a water-in-oil-in-water multiple emulsion and wasprepared by process (vi), using Span 80 as emulsifier #1. Concentratecompositions 29-03 to 29-08 and 29-14, 29-16, & 29-17 are oil-in-wateremulsions and were prepared by process (vii). Concentrate compositions29-09 to 29-13, and 29-15 are aqueous solution concentrates and wereprepared by process (viii).

TABLE 29a % w/w Concentrate Glyphosate Butyl Span % in inner aq. phaseEmulsifier composition a.e. stearate 80 Emulsifier #2 Water Glyphosate#2 29-01 10 18.0 3.0 2.5 9.0 20 Tween 20 29-02 15 1.0 10.0 Emerest 266129-03 15 1.0 10.0 Tween 80 29-04 15 1.0 10.0 oleth-20 29-05 15 1.0 10.0Neodol 25-20 29-06 15 1.0 10.0 ceteareth-27 29-07 15 1.0 10.0ceteareth-55 29-08 15 1.0 10.0 Genapol UD-110 29-09 15 10.0 ceteareth-2729-10 15 10.0 ceteareth-55 29-11 15 10.0 Genapol UD-110 29-12 15 10.0oleth-20 29-13 10 10.0 oleth-20 29-14 10 1.0 10.0 oleth-20 29-15 20 10.0oleth-20 29-16 15 0.5 5.0 oleth-20 29-17 15 0.5 10.0 oleth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 29b.

TABLE 29b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 0 0 250 8 20 350 27 40 450 62 50Formulation C 150 27 50 250 75 70 350 92 80 450 97 92 Formulation J 15023 30 250 72 50 350 94 63 450 95 80 29-01 150 22 30 250 60 40 350 83 57450 90 67 29-02 150 12 33 250 45 50 350 73 63 450 83 83 29-03 150 27 43250 68 50 350 80 63 450 87 87 29-04 150 68 47 250 95 73 350 99 78 450 9590 29-05 150 50 50 250 77 77 350 90 83 450 98 83 29-06 150 78 67 250 9382 350 97 87 450 99 97 29-07 150 87 57 250 96 73 350 99 85 450 99 9729-08 150 42 30 250 73 53 350 82 85 450 95 89 29-09 150 67 40 250 95 73350 99 95 450 99 98 29-10 150 85 60 250 96 68 350 96 91 450 100 88 29-11150 13 10 250 67 50 350 78 60 450 88 73 29-12 150 72 43 250 97 68 350 9883 450 99 93 29-13 150 73 57 250 88 70 350 98 87 450 99 96 29-14 150 8050 250 96 70 350 99 85 450 98 88 29-15 150 70 43 250 96 53 350 97 82 45099 89 29-16 150 62 53 250 88 72 350 99 81 450 99 91 29-17 150 72 58 25095 68 350 100 89 450 100 93

The greatest herbicidal effectiveness in this test was exhibited bycompositions containing a C₁₆₋₁₈ alkylether surfactant (oleth-20,ceteareth-27 or ceteareth-55).

Example 30

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 30a. All areoil-in-water emulsions and were prepared by process (vii).

TABLE 30a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 30-01 163 1.00 10.0 Tween 80 30-02163 1.00 10.0 Emerest 2661 30-03 326 1.00 10.0 Genapol UD-110 30-04 3260.50 10.0 Genapol UD-110 30-05 326 0.25 10.0 Genapol UD-110 30-06 1630.25 10.0 Genapol UD-110 30-07 163 1.00 10.0 Genapol UD-110 30-08 1631.00 10.0 Neodol 1-9 30-09 163 1.00 10.0 Neodol 1-12 30-10 163 1.00 10.0Neodol 25-20 30-11 163 1.00 10.0 Neodol 25-12 30-12 163 1.00 10.0 Neodox25-11 30-13 163 1.00 10.0 laureth-23 30-14 163 1.00 10.0 ceteth-20 30-15163 1.00 10.0 steareth-20 30-16 163 1.00 10.0 oleth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 15 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 23 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 30b.

TABLE 30b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 0 0 250 25 22 350 60 40 450 65 52Formulation C 150 43 52 250 72 83 350 87 98 450 97 95 Formulation J 15050 43 250 75 91 350 86 96 450 95 97 30-01 150 50 30 250 75 75 350 85 87450 90 92 30-02 150 35 47 250 58 77 350 75 85 450 80 96 30-03 150 33 32250 57 53 350 75 78 450 84 94 30-04 150 20 25 250 55 68 350 78 91 450 8297 30-05 150 37 12 250 58 42 350 81 70 450 86 73 30-06 150 50 8 250 6540 350 81 65 450 92 85 30-07 150 50 30 250 63 48 350 84 68 450 98 8430-08 150 43 35 250 52 65 350 73 85 450 84 85 30-09 150 55 40 250 68 58350 79 65 450 97 73 30-10 150 69 40 250 81 68 350 94 92 450 99 96 30-11150 58 50 250 84 60 350 90 83 450 94 93 30-12 150 50 40 250 57 67 350 6584 450 75 98 30-13 150 57 53 250 78 73 350 89 97 450 98 97 30-14 150 6867 250 85 73 350 97 98 450 100 97 30-15 150 72 50 250 88 89 350 89 98450 99 97 30-16 150 65 53 250 87 72 350 97 85 450 100 95

Activity overall in this test was very high, and differences amongcompositions in herbicidal effectiveness are difficult to discernclearly.

Example 31

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 31a. All areoil-in-water emulsions and were prepared by process (vii).

TABLE 31a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 31-01 163 1.00 10.0 Tween 80 31-02163 1.00 10.0 Emerest 2661 31-03 163 1.00 10.0 Neodol 25-20 31-04 1631.00 10.0 oleth-20 31-05 163 0.50 5.0 oleth-20 31-06 163 0.25 2.5oleth-20 31-07 163 0.50 2.5 oleth-20 31-08 163 0.50 1.0 oleth-20 31-09163 0.25 5.0 oleth-20 31-10 326 1.00 10.0 Neodol 1-12 31-11 326 0.5010.0 Neodol 1-12 31-12 326 0.25 10.0 Neodol 1-12 31-13 326 1.00 5.0Neodol 1-12 31-14 326 0.50 5.0 Neodol 1-12 31-15 326 0.25 5.0 Neodol1-12 31-16 326 0.10 5.0 Neodol 1-12

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 15 days after planting ABUTH and ECHEF, and evaluation ofherbicidal inhibition was done 20 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 31b.

TABLE 31b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 7 50 250 45 60 350 73 73 450 80 78Formulation C 150 75 77 250 87 100 350 96 99 450 99 97 Formulation J 15072 77 250 83 89 350 97 99 450 97 98 31-01 150 60 75 250 80 85 350 93 97450 98 98 31-02 150 57 75 250 70 83 350 87 83 450 90 94 31-03 150 77 80250 87 92 350 97 87 450 99 98 31-04 150 80 89 250 93 92 350 99 99 450100 99 31-05 150 83 83 250 92 93 350 97 90 450 100 93 31-06 150 77 77250 80 91 350 90 99 450 98 99 31-07 150 77 83 250 82 89 350 90 91 450 9798 31-08 150 47 82 250 73 82 350 80 97 450 92 91 31-09 150 73 78 250 8788 350 97 94 450 99 99 31-10 150 52 67 250 70 80 350 93 88 450 93 9431-11 150 40 68 250 72 85 350 87 96 450 93 96 31-12 150 37 60 250 68 83350 85 85 450 93 75 31-13 150 28 63 250 53 80 350 85 97 450 88 97 31-14150 37 63 250 58 73 350 83 96 450 90 91 31-15 150 30 70 250 47 83 350 8289 450 87 89 31-16 150 40 53 250 53 82 350 80 80 450 88 77

Composition 31-04, containing 1% butyl stearate and 10% oleth-20(surfactant to glyphosate a.e. weight/weight ratio about 1:1.5),exhibited marginally greater herbicidal effectiveness than composition31-03, containing 1% butyl stearate and 10% Neodol 25-20. At this veryhigh surfactant to glyphosate ratio, however, both performed extremelywell. Surprisingly, when the butyl stearate and oleth-20 concentrationswere significantly lowered, this high level of performance wasmaintained to a remarkable degree. Even when butyl stearate was reducedto 0.25% and oleth-20 to 2.5% (surfactant to glyphosate a.e. ratio about1:6), as in composition 31-06, herbicidal effectiveness was stillsimilar to that obtained with commercial standard Formulations C and J.

Example 32

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 32a. Concentratecompositions 32-01 to 32-08 and 32-11 to 32-16 are oil-in-wateremulsions and were prepared by process (vii). Concentrate compositions32-09 and 32-10 are aqueous solution concentrates and were prepared byprocess (viii).

TABLE 32a % w/w Concentrate Glyphosate Butyl Type of composition a.e.stearate Surfactant surfactant 32-01 15.0 0.25 5.0 Emerest 2661 32-0215.0 0.25 5.0 Tween 80 32-03 15.0 0.25 5.0 Neodol 25-20 32-04 15.0 0.255.0 laureth-23 32-05 15.0 0.25 5.0 ceteth-20 32-06 15.0 0.25 2.5 Tween80 32-07 15.0 0.10 1.0 Tween 80 32-08 15.0 1.00 10.0 Tween 80 32-09 15.05.0 laureth-23 32-10 15.0 5.0 ceteth-20 32-11 15.0 1.00 10.0 Neodol25-20 32-12 15.0 1.00 10.0 oleth-20 32-13 15.0 0.50 5.0 oleth-20 32-1415.0 0.25 5.0 oleth-20 32-15 15.0 0.25 2.5 oleth-20 32-16 15.0 0.25 5.0Genapol UD-110

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 12 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 16 days after application.

Formulaitons B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 32b.

TABLE 32b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 2 10 250 5 20 350 43 30 450 58 43Formulation C 150 68 50 250 92 79 350 96 90 450 98 85 Formulation J 15057 43 250 90 63 350 95 80 450 95 95 32-01 150 7 33 250 50 43 350 77 53450 80 93 32-02 150 17 50 250 72 70 350 80 80 450 80 93 32-03 150 43 40250 75 68 350 87 75 450 96 95 32-04 150 33 47 250 73 63 350 80 77 450 9093 32-05 150 73 37 250 92 57 350 95 88 450 95 73 32-06 150 25 35 250 6847 350 80 92 450 88 85 32-07 150 3 30 250 57 40 350 77 53 450 80 6732-08 150 53 43 250 77 62 350 80 88 450 93 80 32-09 150 32 60 250 77 53350 93 73 450 97 93 32-10 150 75 35 250 92 77 350 96 77 450 97 93 32-11150 75 53 250 90 78 350 95 89 450 98 97 32-12 150 80 43 250 95 73 350 9692 450 98 89 32-13 150 75 53 250 92 97 350 97 99 450 96 93 32-14 150 7870 250 90 92 350 93 97 450 95 93 32-15 150 70 60 250 83 98 350 95 99 45097 99 32-16 150 27 52 250 75 73 350 80 98 450 83 99

Extremely high herbicidal effectiveness was again observed with acomposition (32-15) containing 15% glyphosate a.e. and just 2.5%oleth-20 together with 0.25% butyl stearate. A comparison of 15%glyphosate a.e. compositions containing 5% alkylether surfactant and0.25% butyl stearate provided the following ranking of alkylethers indescending order of effectiveness: oleth-20 (32-14)>ceteth-20(32-05)>Neodol 25-20 (32-03)=laureth-23 (67-04).

Example 33

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 33a. All areoil-in-water emulsions and were prepared by process (vii).

TABLE 33a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 33-01 163 0.50 5.0 oleth-20 33-02163 0.25 5.0 oleth-20 33-03 163 0.25 2.5 oleth-20 33-04 163 1.00 10.0oleth-20 33-05 163 0.50 5.0 steareth-20 33-06 163 0.25 5.0 steareth-2033-07 163 0.25 2.5 steareth-20 33-08 163 1.00 10.0 steareth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 14 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 16 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 33b.

TABLE 33b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 0 30 250 20 43 350 43 53 450 68 57Formulation C 150 60 47 250 75 53 350 87 80 450 87 78 Formulation J 15042 43 250 83 60 350 87 73 450 93 87 33-01 150 60 60 250 78 63 350 87 89450 92 78 33-02 150 70 43 250 80 91 350 87 86 450 96 87 33-03 150 52 43250 75 72 350 83 93 450 87 94 33-04 150 72 50 250 93 73 350 97 95 450 9791 33-05 150 72 43 250 80 78 350 87 91 450 93 85 33-06 150 68 40 250 8050 350 93 75 450 95 85 33-07 150 63 37 250 78 55 350 87 84 450 83 8233-08 150 70 50 250 80 70 350 92 84 450 94 98

All compositions containing butyl stearate and either oleth-20 orsteareth-20 showed a very high level of performance by comparison withcommercial standard Formulations C and J.

Example 34

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 34a. All areoil-in-water emulsions and were prepared by process (vii).

TABLE 34a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 34-01 163 0.50 5.0 oleth-20 34-02163 0.25 5.0 oleth-20 34-03 163 0.25 2.5 oleth-20 34-04 163 1.00 10.0oleth-20 34-05 163 0.50 5.0 steareth-20 34-06 163 0.25 5.0 steareth-2034-07 163 0.25 2.5 steareth-20 34-08 163 1.00 10.0 steareth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 34b.

TABLE 34b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 3 10 250 28 23 350 72 37 450 73 50Formulation C 150 57 43 250 87 62 350 93 83 450 99 95 Formulation J 15027 47 250 70 53 350 92 75 450 94 92 34-01 150 68 50 250 85 47 350 97 70450 99 83 34-02 150 67 40 250 78 50 350 96 63 450 99 68 34-03 150 52 40250 72 50 350 95 63 450 97 85 34-04 150 72 40 250 97 53 350 97 77 450 9990 34-05 150 75 40 250 0 53 350 88 53 450 96 78 34-06 150 98 40 250 9350 350 97 68 450 97 82 34-07 150 73 40 250 92 50 350 98 63 450 98 8034-08 150 77 43 250 93 57 350 97 77 450 98 88

All compositions containing butyl stearate and either oleth-20 orsteareth-20 showed a very high level of performance by comparison withcommercial standard Formulations C and J.

Example 35

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 35a. Concentratecomposition 35-03 is an aqueous solution concentrate and was prepared byprocess (viii). Concentrate compositions 35-01, 35-02 and 35-04 to 35-09are aqueous solution concentrates containing colloidal particulate andwere prepared by process (ix).

TABLE 35a Gly- % w/w Concentrate phosate Butyl Ethomeen Neodol PG-Aluminum composition g a.e./l stearate T/25 1-7 2069 oxide C 35-01 4840.4 35-02 484 5.0 0.4 35-03 484 5.0 35-04 484 6.0 1.0 0.4 35-05 484 7.02.0 0.4 35-06 484 0.3 6.0 1.0 0.4 35-07 484 4.0 1.0 0.4 35-08 484 5.02.0 0.4 35-09 484 0.3 4.0 1.0 0.4

Velvet leaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 14 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 17 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 35b.

TABLE 35b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 0 23 250 38 30 350 65 40 450 75 40Formulation J 150 65 50 250 77 80 350 93 93 450 98 94 35-01 150 58 33250 65 40 350 78 43 450 78 47 35-02 150 32 20 250 63 33 350 72 40 450 8347 35-03 150 67 43 250 93 75 350 93 84 450 100 87 35-04 150 72 43 250 9482 350 98 89 450 100 95 35-05 150 63 40 250 77 60 350 97 83 450 99 8235-06 150 70 40 250 78 72 350 98 83 450 99 93 35-07 150 65 78 250 87missing 350 88 89 450 99 95 35-08 150 73 63 250 78 88 350 82 94 450 8277 35-09 150 58 55 250 78 83 350 88 86 450 99 91

The addition of butyl stearate did not enhance herbicidal effectivenessof the compositions of this Example (compare 35-06 with 35-04 and 35-09with 35-07).

Example 36

Aqueous spray compositions were prepared containing glyphosate IPA saltand excipient ingredients as shown in Table 36a. Process (iii) wasfollowed for spray compositions 36-01 to 36-22 and 36-26 to 36-72, usingsoybean lecithin (45% phospholipid, Avanti). Process (i) was followedfor spray compositions 36-23 to

TABLE 36a Spray % w/w composition Lecithin Butyl stearate MON 0818 36-010.10 0.10 36-02 0.10 0.08 36-03 0.10 0.05 36-04 0.10 0.03 36-05 0.100.01 36-06 0.08 0.10 36-07 0.05 0.10 36-08 0.03 0.10 36-09 0.01 0.1036-10 0.08 0.01 36-11 0.05 0.01 36-12 0.03 0.01 36-13 0.01 0.01 36-140.01 0.03 36-15 0.01 0.05 36-16 0.01 0.08 36-17 0.03 0.03 36-18 0.050.05 36-19 0.08 0.08 36-20 0.08 0.03 36-21 0.03 0.08 36-22 0.05 36-230.05 36-24 0.09 36-25 0.03 36-26 0.09 0.02 0.09 36-27 0.09 0.02 0.0536-28 0.01 0.01 0.01 36-29 0.01 0.01 0.03 36-30 0.01 0.01 0.05 36-310.01 0.01 0.08 36-32 0.01 0.01 0.10 36-33 0.01 0.05 0.01 36-34 0.01 0.050.03 36-35 0.01 0.05 0.05 36-36 0.01 0.05 0.08 36-37 0.01 0.05 0.1036-38 0.01 0.10 0.01 36-39 0.01 0.10 0.03 36-40 0.01 0.10 0.05 36-410.01 0.10 0.08 36-42 0.01 0.10 0.10 36-43 0.05 0.01 0.01 36-44 0.05 0.010.03 36-45 0.05 0.01 0.05 36-46 0.05 0.01 0.08 36-47 0.05 0.01 0.1036-48 0.05 0.05 0.01 36-49 0.05 0.05 0.03 36-50 0.05 0.05 0.05 36-510.05 0.05 0.08 36-52 0.05 0.05 0.10 36-53 0.05 0.10 0.01 36-54 0.05 0.100.03 36-55 0.05 0.10 0.05 36-56 0.05 0.10 0.08 36-57 0.05 0.10 0.1036-58 0.10 0.01 0.01 36-59 0.10 0.01 0.03 36-60 0.10 0.01 0.05 36-610.10 0.01 0.08 36-62 0.10 0.01 0.10 36-63 0.10 0.05 0.01 36-64 0.10 0.050.03 36-65 0.10 0.05 0.05 36-66 0.10 0.05 0.08 36-67 0.10 0.05 0.1036-68 0.10 0.10 0.01 36-69 0.10 0.10 0.03 36-70 0.10 0.10 0.05 36-710.10 0.10 0.08 36-72 0.10 0.10 0.10

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 15 days after application.

Formulations C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 36b.

TABLE 36b Glyphosate rate % Inhibition Spray composition g a.e./ha ABUTHECHCF Formulation C 280 71 73 Formulation J 280 65 77 36-01 280 60 4936-02 280 46 47 36-03 280 34 48 36-04 280 33 35 36-05 280 50 33 36-06280 49 52 36-07 280 39 42 36-08 280 48 38 36-09 280 51 42 36-10 280 3730 36-11 280 48 30 36-12 280 56 34 36-13 280 41 45 36-14 280 52 56 36-15280 38 40 36-16 280 53 33 36-17 280 45 40 36-18 280 52 38 36-19 280 3734 36-20 280 36 28 36-21 280 40 38 36-22 280 44 47 36-23 280 60 42 36-24280 92 76 36-25 280 87 69 36-26 280 89 88 36-27 280 79 80 36-28 280 7473 36-29 280 91 76 36-30 280 94 92 36-31 280 87 81 36-32 280 93 77 36-33280 88 73 36-34 280 92 85 36-35 280 90 82 36-36 280 92 77 36-37 280 8777 36-38 280 88 77 36-39 280 84 74 36-40 280 87 68 36-41 280 93 76 36-42280 94 78 36-43 280 80 59 36-44 280 69 54 36-45 280 88 74 36-46 280 9479 36-47 280 95 79 36-48 280 71 63 36-49 280 81 72 36-50 280 81 79 36-51280 79 85 36-52 280 98 69 36-53 280 69 70 36-54 280 74 69 36-55 280 8478 36-56 280 86 68 36-57 280 98 82 36-58 280 71 69 36-59 280 95 79 36-60280 92 70 36-61 280 93 70 36-62 280 98 80 36-63 280 81 74 36-64 280 8473 36-65 280 89 70 36-66 280 91 65 36-67 280 94 81 36-68 280 87 81 36-69280 72 79 36-70 280 87 76 36-71 280 94 71 36-72 280 97 73

Compositions outperforming commercial standard Formulations C and J onboth ABUTH and ECHCF in this test included 36-26, 36-27, 36-30, 36-34,36-35, 36-51 and 36-57, all containing lecithin, butyl stearate and MON0818.

Example 37

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 37a. All containcolloidal particulates and were prepared by process (ix).

All compositions of this example showed acceptable storage stability.The compositions containing oleth-20 were not acceptably storage-stablein the absence of the colloidal particulate.

TABLE 37a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Oleth-20 Aerosil Aerosil 37-01 488 3.0 0.4 OX-50 37-02488 3.0 0.8 OX-50 37-03 488 3.0 1.5 OX-50 37-04 488 0.4 OX-50 37-05 4880.8 OX-50 37-06 488 1.5 OX-50 37-07 488 3.0 0.4 MOX-80 37-08 488 3.0 0.8MOX-80 37-09 488 3.0 1.5 MOX-80 37-10 488 0.4 MOX-80 37-11 488 0.8MOX-80 37-12 488 1.5 MOX-80 37-13 488 3.0 0.4 MOX-170 37-14 488 3.0 0.8MOX-170 37-15 488 3.0 1.5 MOX-170 37-16 488 0.4 MOX-170 37-17 488 0.8MOX-170 37-18 488 1.5 MOX-170 37-19 488 3.0 3.0 1.5 MOX-80

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 14 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 20 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 37b.

TABLE 37b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 0 27 250 17 37 350 47 57 450 60 60Formulation J 150 57 50 250 82 87 350 95 99 450 98 99 37-01 150 37 60250 73 70 350 96 97 450 96 99 37-02 150 43 50 250 73 63 350 93 96 450 9899 37-03 150 53 60 250 83 87 350 87 97 450 98 98 37-04 150 45 40 250 5760 350 78 95 450 94 100 37-05 150 47 50 250 60 82 350 92 96 450 95 9937-06 150 38 53 250 68 96 350 82 99 450 83 95 37-07 150 50 57 250 87 88350 91 99 450 98 98 37-08 150 53 50 250 88 85 350 96 97 450 97 100 37-09150 40 30 250 37 47 350 57 80 450 77 94 37-10 150 47 50 250 70 95 350 7599 450 77 98 37-11 150 27 60 250 72 85 350 82 98 450 75 99 37-12 150 3757 250 73 86 350 80 99 450 85 100 37-13 150 45 53 250 85 94 350 95 100450 98 99 37-14 150 50 50 250 78 83 350 94 98 450 98 99 37-15 150 53 67250 75 88 350 93 97 450 96 99 37-16 150 42 50 250 47 96 350 70 98 450 9099 37-17 150 27 83 250 57 98 350 87 99 450 87 100 37-18 150 33 60 250 4794 350 83 99 450 93 99 37-19 150 45 47 250 80 73 350 96 94 450 99 98

Remarkably high levels of herbicidal effectiveness were obtained in thistest with compositions containing oleth-20 at a weight/weight ratio toglyphosate a.e. of about 1:14, and stabilized with colloidalparticulates. In some cases the colloidal particulate alone contributeda major part of the efficacy enhancement. Composition 37-19, containingbutyl stearate, was among the most efficacious compositions in the test.Results with composition 37-09 are out of line with other data and anapplication problem is suspected.

Example 38

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 38a. All were preparedby process (x), using soybean lecithin (45% phospholipid, Avanti).

TABLE 38a % w/w Concentrate Glyphosate Butyl Ethomeen composition ga.e./l Lecithin stearate T/25 38-01 200 6.0 2 6.0 38-02 200 3 6.0 38-03200 1.5 9.0 38-04 200 3 9.0 38-05 200 6.0 1.5 9.0 38-06 200 6.0 1.5 3.038-07 200 9.0

Velvetleaf (Abutilon Theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 15 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 38b.

TABLE 38b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 29 22 250 41 29 350 53 32 450 68 35Formulation J 150 43 32 250 76 43 350 86 47 450 94 66 38-01 150 67 33250 85 40 350 96 71 450 97 59 38-02 150 65 36 250 81 52 350 97 68 450 9862 38-03 150 67 40 250 85 77 350 94 77 450 97 63 38-04 150 69 38 250 8658 350 93 84 450 98 62 38-05 150 73 40 250 83 53 350 93 75 450 96 6138-06 150 45 30 250 71 38 350 91 45 450 89 39 38-07 15o 59 39 250 83 44350 95 63 450 95 70

Data for the 450 g a.e./ha glyphosate rate in this study are unreliable.Application error is suspected. The high levels of Ethomeen T/25included in compositions of this Example tends to obscure the effects oflecithin and butyl stearate, but composition 38-05, for example, showedoutstanding effectiveness.

Example 39

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 39a. Concentratecompositions 39-01 to 39-04, 39-06, 39-08, 39-09, 39-11, 39-12, 39-14and 39-16 are oil-in-water emulsions and were prepared by process (vii).Concentrate compositions 39-05, 39-07, 39-10, 39-13, 39-15 and 39-17 areaqueous solution concentrates and were prepared by process (viii).

TABLE 39a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 39-01 163 0.25 2.5 Neodol 1-1239-02 163 0.25 2.5 laureth-23 39-03 163 0.25 2.5 steareth-10 39-04 1630.25 2.5 steareth-20 39-05 163 2.5 steareth-20 39-06 163 0.25 2.5steareth-100 39-07 163 2.5 steareth-100 39-08 163 0.25 2.5 oleth-1039-09 163 0.25 2.5 oleth-20 39-10 163 2.5 oleth-20 39-11 163 0.25 2.5ceteth-10 39-12 163 0.25 2.5 ceteth-20 39-13 163 2.5 ceteth-20 39-14 3260.50 5.0 ceteareth-27 39-15 326 5.0 ceteareth-27 39-16 163 0.25 2.5ceteareth-55 39-17 163 2.5 ceteareth-55

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 15 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 39b.

TABLE 39b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 33 250 20 43 350 63 63 450 75 70Formulation C 150 53 55 250 80 87 350 94 97 450 98 99 Formulation J 15040 57 250 80 90 350 96 99 450 98 99 39-01 150 52 40 250 65 73 350 77 70450 77 70 39-02 150 37 70 250 75 80 350 83 97 450 95 99 39-03 150 47 53250 77 86 350 83 97 450 93 100 39-04 150 80 60 250 93 83 350 96 85 45099 99 39-05 150 80 43 250 93 79 350 96 94 450 98 96 39-06 150 77 53 25085 83 350 94 99 450 97 99 39-07 150 63 50 250 80 88 350 85 96 450 96 9939-08 150 27 45 250 75 83 350 77 99 450 96 98 39-09 150 75 57 250 80 82350 97 95 450 99 98 39-10 150 70 40 250 85 83 350 97 98 450 99 99 39-11150 53 37 250 75 63 350 88 93 450 92 98 39-12 150 70 40 250 78 75 350 9091 450 98 98 39-13 150 72 40 250 92 80 350 97 90 450 99 97 39-14 150 7853 250 89 88 350 97 95 450 99 100 39-15 150 80 60 250 95 97 350 98 100450 99 99 39-16 150 60 63 250 87 78 350 96 94 450 98 99 39-17 150 73 60250 85 57 350 93 80 450 99 85

In combination with butyl stearate, steareth-20 (composition 39-04) gavegreater herbicidal effectiveness than steareth-10 (39-03) on ABUTH.Similarly, oleth-20 (39-09) was more efficacious than oleth-10 (39-08)and ceteth-20 (39-12) than ceteth-10 (39-11). In the absence of butylstearate, ceteareth-55 (39-17) was noticeably weaker on ECHCF thanceteareth-27 (39-15) but inclusion of butyl stearate (39-16) tended tocorrect this weakness. Note that while compositions 39-14 and 39-15contained twice as high a concentration of excipients as the othercompositions of the test, the concentration of glyphosate was also twiceas high, thus the concentrations as sprayed were the same.

Example 40

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 40a. Concentratecompositions 40-01 to 40-05, 40-07, 40-08, 40-10 and 40-12 to 40-16 areoil-in-water emulsions and were prepared by process (vii). Concentratecompositions 40-06, 40-09 and 40-11 are aqueous solution concentratesand were prepared by process (viii).

TABLE 40a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 40-01 163 0.25 2.5 Neodol 1-1240-02 163 0.25 2.5 laureth-23 40-03 163 0.25 2.5 steareth-10 40-04 1630.25 2.5 steareth-20 40-05 163 0.25 2.5 Pluronic F-68 40-06 163 2.5Pluronic F-68 40-07 326 1.00 5.0 Pluronic F-108 40-08 326 0.50 5.0Pluronic F-108 40-09 326 5.0 Pluronic F-108 40-10 163 0.25 2.5 PluronicF-127 40-11 163 2.5 Pluronic F-127 40-12 326 0.50 5.0 ceteareth-27 40-13163 0.25 2.5 ceteareth-55 40-14 163 0.25 2.5 oleth-20 40-15 163 0.25 2.5ceteth-20 40-16 163 0.25 2.5 steareth-100

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 15 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 40b.

TABLE 40b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 5 0 250 47 5 350 70 23 450 75 43Formulation C 150 73 47 250 99 50 350 98 67 450 99 75 Formulation J 15073 43 250 89 50 350 97 83 450 98 77 40-01 150 37 30 250 70 33 350 77 40450 90 47 40-02 150 52 37 250 77 67 350 90 77 450 92 75 40-03 150 40 30250 77 70 350 80 82 450 90 83 40-04 150 75 37 250 95 53 350 99 91 450 9982 40-05 150 58 37 250 65 53 350 80 80 450 75 68 40-06 150 40 30 250 7533 350 78 43 450 80 43 40-07 150 50 30 250 75 33 350 78 53 450 86 5340-08 150 47 30 250 75 33 350 77 40 450 80 50 40-09 150 43 33 250 77 40350 78 63 450 83 50 40-10 150 27 40 250 77 43 350 80 50 450 92 40 40-11150 37 30 250 72 33 350 80 60 450 95 40 40-12 150 78 37 250 98 40 350 9953 450 100 50 40-13 150 75 30 250 88 40 350 98 47 450 100 65 40-14 15073 30 250 87 40 350 98 50 450 99 53 40-15 150 72 30 250 93 40 350 96 43450 99 5o 40-16 150 73 40 250 83 40 350 98 40 450 100 47

Composition 40-04 containing steareth-20 outperformed its counterpart40-03 containing steareth-10, though both gave greater herbicidaleffectiveness, especially on ECHCF, than 40-02 containing laureth-23 or40-01 containing Neodol 1-12.

Example 41

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 41a. Concentratecompositions 41-01 to 41-07 and 41-09 to 41-15 are oil-in-wateremulsions and were prepared by process (vii). Concentrate compositions41-08 and 41-16 are aqueous solution concentrates and were prepared byprocess (viii).

TABLE 41a Glypho- Concentrate sate % w/w Type of Type of composition ga.e./l Oil Surfactant oil surfactant 41-01 163 0.5 5.0 methyl stearateoleth-20 41-02 163 0.5 5.0 butyl stearate oleth-20 41-03 163 0.5 5.0methyl oleate oleth-20 41-04 163 0.5 5.0 butyl oleate oleth-20 41-05 1630.5 5.0 methyl laurate oleth-20 41-06 163 0.5 5.0 butyl laurate oleth-2041-07 163 0.5 5.0 Orchex 796 oleth-20 41-08 163 5.0 none oleth-20 41-09163 0.5 5.0 methyl stearate Neodol 1-9 41-10 163 0.5 5.0 butyl stearateNeodol 1-9 41-11 163 0.5 5.0 methyl oleate Neodol 1-9 41-12 163 0.5 5.0butyl oleate Neodol 1-9 41-13 163 0.5 5.0 methyl laurate Neodol 1-941-14 163 0.5 5.0 butyl laurate Neodol 1-9 41-15 163 0.5 5.0 Orchex 796Neodol 1-9 41-16 163 5.0 none Neodol 1-9

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 19 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 41b.

TABLE 41b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 3 10 250 58 57 350 78 53 450 77 53Formulation C 150 60 98 250 87 99 350 95 98 450 99 100 Formulation J 15060 75 250 89 87 350 93 90 450 98 99 41-01 150 75 96 250 99 97 350 97 99450 99 100 41-02 150 60 60 250 97 67 350 99 98 450 100 95 41-03 150 6340 250 83 82 350 97 86 450 97 88 41-04 150 73 40 250 94 82 350 97 100450 99 100 41-05 150 67 47 250 86 67 350 97 88 450 99 100 41-06 150 6043 250 78 91 350 97 83 450 94 86 41-07 150 70 53 250 80 53 350 97 82 45097 92 41-08 150 70 62 250 83 83 350 91 87 450 98 98 41-09 150 45 42 25072 72 350 77 73 450 78 89 41-10 150 40 30 250 82 80 350 78 98 450 89 9341-11 150 40 30 250 65 60 350 77 90 450 96 92 41-12 150 20 30 250 63 73350 80 75 450 93 86 41-13 150 20 27 250 67 60 350 82 91 450 88 92 41-14150 7 30 250 72 81 350 87 78 450 80 85 41-15 150 20 23 250 65 60 350 7781 450 87 88 41-16 150 12 30 250 57 53 350 68 85 450 85 85

Composition 41-08, containing as sole excipient substance oleth-20 at a1:3 weight/weight ratio to glyphosate a.e., exhibited high herbicidaleffectiveness, at least equal to commercial standard Formulations C andJ on ABUTH but a little weaker on ECHCF. By comparison, composition41-16, wherein the sole excipient substance was Neodol 1-9 at the sameratio to glyphosate, had much weaker activity. Addition of a smallamount of fatty acid ester in most cases enhanced effectiveness,especially on ECHCF. In this study the most efficacious composition was41-01, containing oleth-20 and methyl stearate. When added to Neodol1-9, butyl stearate was more efficacious than methyl stearate, methyloleate or butyl oleate. The mineral oil Orchex 796 did not substituteeffectively for butyl stearate, either with oleth-20 or with Neodol 1-9.

Example 42

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 42a. Concentratedcompositions 42-01, 42-03, 42-05 to 42-08, 42-10 and 42-14 to 42-17 areoil-in-water emulsions and were prepared by process (vii). Concentratecompositions 42-02, 42-04, 42-09 and 42-11 to 42-13 are aqueous solutionconcentrates and were prepared by process (viii). Some compositionscontained a coupling agent as indicated in Table 42a; the coupling agentwas added with the surfactant.

TABLE 42a % w/w Glypho- Butyl Coup- Type of Conc. sate stear- Sur- lingcoupling Type of comp. g a.e./l ate facant agent agent surfacant 42-01326 1.0 5.0 2.5 Arcosolve oleth-20 DPM 42-02 326 5.0 2.5 Arcosolveoleth-20 DPM 42-03 163 0.5 2.5 none oleth-20 42-04 163 2.5 none oleth-2042-05 326 1.0 5.0 none ceteareth-27 42-06 326 1.0 5.0 2.5 PEG-400ceteareth-27 42-07 326 1.0 5.0 2.5 Dowanol ceteareth-27 TPNB 42-08 3261.0 5.0 2.5 Dowanol ceteareth-27 PNB 42-09 163 2.5 none ceteareth-2742-10 326 0.5 5.0 none ceteareth-27 42-11 326 5.0 2.5 PEG-400ceteareth-27 42-12 326 5.0 2.5 Dowanol ceteareth-27 TPNB 42-13 326 5.02.5 Dowanol ceteareth-27 PNB 42-14 163 0.5 2.5 none Neodol 1-9 42-15 1630.5 2.5 none laureth-23 42-16 163 0.5 2.5 none steareth-20 42-17 163 0.52.5 none ceteareth-27

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 16 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 42b.

TABLE 42b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 0 5 250 38 20 350 63 30 450 70 70Formulation C 150 70 75 250 92 94 350 99 99 450 99 98 Formulation J 15065 50 250 88 92 350 97 99 450 98 97 42-01 150 58 83 250 77 88 350 93 96450 93 99 42-02 150 40 76 250 75 100 350 92 100 450 92 100 42-03 150 4875 250 83 96 350 92 100 450 99 100 42-04 150 40 82 250 78 99 350 87 99450 98 100 42-05 150 68 92 250 87 99 350 95 99 450 99 99 42-06 150 55 60250 83 99 350 97 99 450 98 98 42-07 150 63 57 250 80 96 350 95 97 450 9998 42-08 150 73 75 250 90 90 350 95 97 450 100 97 42-09 150 73 68 250 8773 350 92 90 450 97 95 42-10 150 70 63 250 87 80 350 98 94 450 99 9642-11 150 73 60 250 90 77 350 99 93 450 100 95 42-12 150 72 67 250 83 75350 90 82 450 99 94 42-13 150 73 70 250 80 83 350 99 94 450 100 92 42-14150 5 20 250 55 63 350 77 93 450 78 99 42-15 150 43 57 250 78 88 350 8898 450 90 98 42-16 150 65 57 250 83 82 350 88 98 450 95 97 42-17 150 7250 250 80 93 350 88 90 450 95 97

The superiority of herbicidal effectiveness provided by C₁₆₋₁₈alkylethers (oleth-20, ceteareth-27, steareth-20) over that provided byshorter chain alkylethers (Neodol 1-9, laureth-23) was very pronouncedin this test.

Example 43

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 43a. Concentratecompositions 43-01 to 43-07 and 43-09 to 43-15 are oil-in-wateremulsions and were prepared by process (vii). Concentrate compositions43-08 and 43-16 are aqueous solution concentrates and were prepared byprocess (viii).

TABLE 43a Glypho- Concentrate sate % w/w Type of Type of composition ga.e./l Oil Surfactant oil surfactant 43-01 163 0.5 5.0 methyl stearatesteareth-20 43-02 163 0.5 5.0 butyl stearate steareth-20 43-03 163 0.55.0 methyl oleate steareth-20 43-04 163 0.5 5.0 butyl oleate steareth-2043-05 163 0.5 5.0 methyl laurate steareth-20 43-06 163 0.5 5.0 butyllaurate steareth-20 43-07 163 0.5 5.0 Orchex 796 steareth-20 43-08 1635.0 none steareth-20 43-09 163 0.5 5.0 methyl stearate ceteareth-2743-10 163 0.5 5.0 butyl stearate ceteareth-27 43-11 163 0.5 5.0 methyloleate ceteareth-27 43-12 163 0.5 5.0 butyl oleate ceteareth-27 43-13163 0.5 5.0 methyl laurate ceteareth-27 43-14 163 0.5 5.0 butyl laurateceteareth-27 43-15 163 0.5 5.0 Orchex 796 ceteareth-27 43-16 163 5.0none ceteareth-27

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 43b.

TABLE 43b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 15 5 250 57 20 350 83 50 450 78 73Formulation C 150 65 63 250 87 93 350 92 94 450 98 100 Formulation J 15050 73 250 90 90 350 94 98 450 98 99 43-01 150 72 70 250 88 85 350 96 83450 99 86 43-02 150 73 53 250 83 87 350 97 99 450 97 98 43-03 150 68 33250 87 92 350 93 97 450 98 93 43-04 150 72 50 250 87 88 350 94 86 450 9897 43-05 150 72 67 250 83 82 350 99 97 450 98 98 43-06 150 73 33 250 9583 350 99 95 450 99 88 43-07 150 73 55 250 93 73 350 95 83 450 98 9143-08 150 75 40 250 94 60 350 98 86 450 99 92 43-09 150 77 50 250 90 50350 98 92 450 99 98 43-10 150 72 53 250 92 77 350 96 86 450 99 99 43-11150 72 60 250 87 87 350 97 97 450 97 99 43-12 150 70 57 250 90 90 350 9696 450 98 99 43-13 150 68 40 250 90 77 350 99 95 450 99 98 43-14 150 7733 250 94 70 350 96 82 450 99 93 43-15 150 75 30 250 96 75 350 97 88 45099 92 43-16 150 77 40 250 99 47 350 98 67 450 98 78

Steareth-20 and ceteareth-27, as sole excipient substances (compositions43-08 and 43-16 respectively) provided excellent herbicidaleffectiveness, but further enhancements, especially on ECHCF, wereobtained by inclusion of a small amount of fatty acid ester in thecomposition.

Example 44

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 44a. Process (vii) wasfollowed for concentrate composition 44-08 and process (x) forconcentrate compositions 44-01 to 44-07 and 44-09, using soybeanlecithin (45% phospholipid, Avanti).

TABLE 44a % w/w Concentrate Glyphosate Butyl composition g a.e./lLecithin stearate MON 0818 44-01 220 4.0 6.0 44-02 220 4.0 0.5 6.0 44-03220 4.0 1.0 6.0 44-04 220 4.0 2.0 6.0 44-05 220 2.0 0.5 2.0 44-06 2202.0 0.5 4.0 44-07 220 2.0 0.5 6.0 44-08 220 0.5 6.0 44-09 220 6.0 1.56.0

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B and C were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 44b.

TABLE 44b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 40 59 Formulation B 150 40 59 250 68 61350 90 91 450 93 94 Formulation C 150 74 78 250 93 90 350 97 96 450 10094 44-01 150 79 85 250 93 98 350 96 97 450 97 95 44-02 150 71 87 250 9396 350 96 94 450 98 94 44-03 150 87 99 250 94 100 350 99 97 450 97 9444-04 150 89 100 250 94 99 350 97 98 450 98 95 44-05 150 73 100 250 90100 350 95 98 450 96 94 44-06 150 80 99 250 94 96 350 95 100 450 99 9844-07 150 88 83 250 94 92 350 96 92 450 100 90 44-08 150 81 91 250 92 96350 97 89 450 99 92 44-09 150 90 96 250 93 93 350 95 95 450 94 98

Herbicidal effectiveness overall was very high under the conditions ofthis study but a tendency can be discerned in compositions 44-01 to44-04 for performance to improve as butyl stearate concentrate wasincreased from zero to 2%.

Example 45

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 45a. Concentratecomposition 45-08 to 45-14 are oil-in-water emulsions and were preparedby process (vii). Concentrate compositions 45-15 to 45-17 are aqueoussolution concentrates and were prepared by process (viii). Concentratecompositions 45-01 to 45-07 contain colloidal particulates and wereprepared by process (ix).

Compositions 45-08 to 45-17 (all containing 163 g a.e./l glyphosate)showed acceptable storage stability. However, at a glyphosate loading of400 g a.e./l (as in compositions 45-01 to 45-07) storage-stablecompositions containing 0.5-1% butyl stearate and 5-10% alkylethersurfactant could not be made except with the addition of colloidalparticulate as shown below.

TABLE 45a Glypho- % w/w Concentrate sate Butyl Type of composition ga.e./l stearate Surfacant Aerosil 90 surfacant 45-01 400 1.0 10.0 1.0ceteareth-27 45-02 400 1.0 10.0 1.0 steareth-20 45-03 400 0.5 5.0 1.0ceteareth-27 45-04 400 0.5 5.0 1.0 steareth-20 45-05 400 1.0 5.0 1.0ceteareth-27 45-06 400 1.0 5.0 1.0 steareth-20 45-07 400 1.0 5.0 1.0steareth-30 45-08 163 0.5 5.0 oleth-20 45-09 163 0.5 5.0 steareth-2045-10 163 0.5 5.0 ceteth-20 45-11 163 0.5 5.0 laureth-23 45-12 163 0.55.0 ceteareth-27 45-13 163 0.5 5.0 Neodol 25-12 45-14 163 0.5 5.0 Neodol25-20 45-15 163 5.0 steareth-20 45-16 163 5.0 ceteth-20 45-17 163 5.0laureth-23

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 18 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 19 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 45b.

TABLE 45b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 150 0 40 250 20 60 350 68 82 450 83 96Formulation C 150 68 93 250 93 99 350 100 100 450 100 100 Formulation J150 43 89 250 93 100 350 100 100 450 100 100 45-01 150 78 97 250 96 100350 98 100 450 100 100 45-02 150 91 98 250 100 100 350 100 100 450 100100 45-03 150 90 97 250 99 99 350 100 100 450 100 100 45-04 150 77 98250 100 100 350 100 100 450 100 100 45-05 150 82 93 250 100 99 350 100100 450 100 100 45-06 150 83 85 250 100 99 350 100 100 450 100 100 45-07150 83 87 250 100 100 350 100 100 450 100 100 45-08 150 90 92 250 100100 350 100 100 450 100 100 45-09 150 90 85 250 100 98 350 100 100 450100 100 45-10 150 80 85 250 100 92 350 100 100 450 100 100 45-11 150 8388 250 96 99 350 100 98 450 100 100 45-12 150 93 85 250 100 99 350 100100 450 100 100 45-13 150 72 73 250 92 97 350 100 99 450 100 100 45-14150 72 80 250 99 99 350 100 100 450 100 100 45-15 150 100 93 250 100 99350 100 100 450 100 100 45-16 150 100 98 250 100 100 350 100 100 450 100100 45-17 150 83 83 250 100 99 350 100 99 450 100 99

Outstanding herbicidal effectiveness was provided by compositionscontaining C₁₆₋₁₈ alkylether surfactants (ceteareth-27, steareth-20,steareth-30 , oleth-20, ceteth-20). High-loaded (400 g a.e./l)glyphosate compositions containing a C₁₆₋₁₈ alkylether surfactant, butylstearate and a colloidal particulate (Aerosil 90) to stabilize thecompositions performed especially impressively in this test.

Example 46

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 46a. Process (v) wasfollowed for compositions 46-01 to 46-12, 46-15 and 46-16, and process(x) for compositions 46-13 and 46-14, using soybean lecithin (45%phospholipid, Avanti). Order of addition of ingredients was varied forcertain compositions as indicated below.

TABLE 46a % w/w Concen- Benz- Order trate Gly- alk- Butyl of com-phosate Leci- Fluorad onium stear- MON addition position g/1 a.e. thinFC-754/135 Cl ate 0818 (*) 46-01 345 4.0 0.66 46-02 345 4.0 1.00 46-03347 3.0 3.00 46-04 347 4.0 4.00 46-05 347 4.0 5.00 46-06 345 4.6 4.6046-07 348 4.0 2.0 (754) 1.10 46-08 351 4.0 4.0 (754) 1.00 A 46-09 3463.9 4.2 (754) 1.00 B 46-10 350 4.0 2.0 (135) 1.10 46-11 352 4.0 4.0(135) 1.00 A 46-12 349 4.0 4.0 (135) 1.00 B 46-13 348 4.0 4.0 (754) 0.500.57 46-14 347 4.0 0.50 0.52 46-15 348 3.7 0.48 3.7 46-16 348 4.0 0.584.0 (*) Order of addition: 1st 2nd 3^(rd) 4th 5th A lecithin waterBenzalkonium FC-135/754 glyphosate Cl B glyphosate FC-135/754Benzalkonium water glyphosate Cl

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 21 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 46b.

TABLE 46b Concentrate Glyphosate rate % Inhibition composition g a.e./haABUTH ECHCF Formulation B 100 5 5 200 15 20 300 47 30 400 65 37Formulation J 100 0 8 200 70 37 300 78 70 400 83 73 46-01 100 3 10 20017 27 300 45 37 400 75 40 46-02 100 2 5 200 13 30 300 43 40 400 75 4746-03 100 0 8 200 17 43 300 65 78 400 78 83 46-04 100 2 10 200 30 37 30068 72 400 75 88 46-05 100 2 20 200 25 65 300 63 88 400 82 83 46-06 10010 17 200 25 33 300 47 77 400 83 75 46-07 100 0 10 200 48 30 300 73 37400 83 43 46-08 100 3 10 200 33 30 300 68 37 400 78 40 46-09 100 5 10200 40 27 300 65 50 400 70 57 46-10 100 0 10 200 30 27 300 67 40 400 7340 46-11 100 0 10 200 33 27 300 52 37 400 82 40 46-12 100 0 10 200 40 20300 65 40 400 72 40 46-13 100 0 10 200 40 20 300 60 33 400 78 33 46-14100 0 10 200 7 47 300 28 33 400 43 43 46-15 100 0 13 200 27 33 300 73 53400 77 67 46-16 100 0 13 200 30 37 300 75 47 400 77 68

Most concentrate compositions of this Example showed enhanced glyphosateeffectiveness by comparison with Formulation B but did not equal theefficacy of commercial standard Formulation J in this test.

Example 47

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 47a. Concentratecomposition 47-01 to 47-09, 47-11 to 47-14, 47-16 and 47-17 areoil-in-water emulsions and were prepared by process (vii). Concentratecompositions 47-10 and 47-15 are aqueous solution concentrates and wereprepared by process (viii).

TABLE 47a % w/w Gly- Other Conc. phosate Oleth- sur- Type of Other comp.g a.e./l Oil 20 factant oil surfactant 47-01 163 0.25 2.5 methyl laurate47-02 163 0.25 2.5 methyl myristate 47-03 163 0.25 2.5 methylpalmitoleate 47-04 163 0.25 2.5 methyl palmitate 47-05 163 0.25 2.5methyl linoleate 47-06 163 0.25 2.5 methyl oleate 47-07 163 0.25 2.5methyl stearate 47-08 163 0.25 2.5 ethyl stearate 47-09 163 0.25 2.5butyl stearate 47-10 163 2.5 none 47-11 163 0.25 2.5 methyl MON 0818palmitoleate 47-12 163 0.25 2.5 methyl MON 0818 palmitate 47-13 163 0.252.5 methyl MON 0818 oleate 47-14 163 0.25 2.5 methyl MON 0818 stearate47-15 163 2.5 none MON 0818 47-16 163 0.25 2.5 butyl stearate laureth-2347-17 163 0.25 2.5 butyl stearate Neodol 1-9

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 20 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 16 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 47b.

TABLE 47b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 2 35 200 52 67 300 77 83 400 78 87Formulation C 100 25 77 200 72 99 300 87 100 400 99 100 Formulation J100 13 73 200 70 97 300 90 100 400 97 100 47-01 100 22 55 200 65 86 30078 98 400 89 98 47-02 100 20 63 200 67 91 300 83 99 400 97 100 47-03 10030 75 200 63 98 300 83 99 400 94 100 47-04 100 23 63 200 60 98 300 90 99400 95 100 47-05 100 27 57 200 62 91 300 83 96 400 93 98 47-06 100 23 50200 63 89 300 83 99 400 96 99 47-07 100 25 53 200 65 94 300 83 99 400 9299 47-08 100 13 47 200 53 88 300 89 97 400 95 99 47-09 100 27 53 200 6085 300 83 97 400 97 98 47-10 100 13 53 200 62 94 300 83 97 400 88 9947-11 100 23 60 200 50 90 300 85 98 400 95 99 47-12 100 17 55 200 35 94300 78 98 400 94 99 47-13 100 8 50 200 43 90 300 73 98 400 90 99 47-14100 30 63 200 45 92 300 80 98 400 94 98 47-15 100 20 63 200 70 96 300 8299 400 94 98 47-16 100 18 62 200 62 83 300 80 97 400 97 97 47-17 100 1752 200 58 85 300 75 90 400 95 98

No great or consistent enhancement of herbicidal effectiveness ofglyphosate compositions containing oleth-20 was obtained by adding asmall amount of any of a variety of fatty acid esters in this study(compare 47-10 with 47-01 to 47-09).

Example 48

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 48a. Concentratecomposition 48-01 to 48-09, 48-11 to 48-14, 48-16 and 48-17 areoil-in-water emulsions and were prepared by process (vii). Concentratecompositions 48-10 and 48-15 are aqueous solution concentrates and wereprepared by process (viii).

TABLE 48a % w/w Concentrate Glyphosate Oleth- Other Type of Othercomposition g a.e./l Oil 20 surfactant oil surfactant 48-01 163 0.25 2.5isopropyl myristate 48-02 163 0.25 2.5 ethylmyristate 48-03 163 0.25 2.5methyl palmitate 48-04 163 0.25 2.5 ethyl palmitate 48-O5 163 0.25 2.5ethyl linoleate 48-06 163 0.25 2.5 ethyl oleate 48-07 163 0.25 2.5methyl stearate 48-08 163 0.25 2.5 ethyl stearate 48-09 163 0.25 2.5butyl stearate 48-10 163 2.5 none 48-11 163 0.25 2.5 methyl palmitateMON 0818 48-12 163 0.25 2.5 methyl stearate MON 0818 48-13 163 0.25 2.5ethyl stearate MON 0818 48-14 163 0.25 2.5 ethyloleate MON 0818 48-15163 2.5 none MON 0818 48-16 163 0.25 2.5 butyl stearate laureth-23 48-17163 0.25 2.5 butyl stearate Neodol 1-9

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 48b.

TABLE 48b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 12 33 200 45 43 300 73 63 400 80 63Formulation C 100 43 57 200 75 88 300 95 99 400 100 99 Formulation J 10053 60 200 77 75 300 96 95 400 99 98 48-01 100 35 40 200 73 72 300 83 91400 99 97 48-02 100 38 30 200 70 43 300 87 82 400 96 80 48-03 100 25 27200 68 50 300 90 73 400 96 82 48-04 100 27 27 200 75 50 300 80 73 400 9680 48-05 100 33 27 200 68 43 300 83 70 400 97 91 48-06 100 33 28 200 7253 300 83 60 400 99 70 48-07 100 37 25 200 72 40 300 83 50 400 97 6548-08 100 32 25 200 73 43 300 87 60 400 98 67 48-09 100 35 25 200 75 43300 95 57 400 98 63 48-10 100 35 27 200 73 40 300 83 76 400 97 73 48-11100 35 33 200 67 67 300 80 86 400 92 70 48-12 100 25 30 200 67 70 300 8376 400 88 80 48-13 100 27 33 200 70 66 300 78 63 400 93 60 48-14 100 3330 200 67 47 300 80 70 400 92 77 48-15 100 20 30 200 68 40 300 83 75 40090 72 48-16 100 30 25 200 62 43 300 73 73 400 77 70 48-17 100 30 23 20058 40 300 75 60 400 80 73

In this study, isopropyl myristate (composition 48-01) was the mosteffective of the fatty acid esters tested as additives to oleth-20(48-10) in glyphosate compositions

Example 49

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 49a. Concentratecomposition 49-01 to 49-09 are oil-in-water emulsions and were preparedby process (vii). Concentrate compositions 49-14 to 49-17 are aqueoussolution concentrates and were prepared by process (viii).

TABLE 49a Concentrate Glyphosate % w/w Type of Type of composition ga.e./l Oil Surfactant oil surfactant 49-01 163 0.25 2.5 butyl stearatelaureth-23 49-02 163 0.25 2.5 butyl stearate steareth-20 49-03 163 0.252.5 butyl stearate ceteareth-20 49-04 163 0.25 2.5 butyl stearateceteareth-15 49-05 163 0.25 2.5 butyl stearate Neodol 44-13 49-06 1630.25 2.5 methyl stearate steareth-20 49-07 163 0.25 2.5 methyl stearateceteareth-20 49-08 163 0.25 2.5 methyl stearate ceteareth-15 49-09 1630.25 2.5 methyl stearate Neodol 44-13 49-10 163 0.25 2.5 methylpalmitate steareth-20 49-11 163 0.25 2.5 methyl palmitate ceteareth-2049-12 163 0.25 2.5 methyl palmitate ceteareth-15 49-13 163 0.25 2.5methyl palmitate Neodol 44-13 49-14 163 2.5 none steareth-20 49-15 1632.5 none ceteareth-20 49-16 163 2.5 none ceteareth-15 49-17 163 2.5 noneNeodol 44-13

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 24 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 16 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 49b.

TABLE 49b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 10 37 200 30 40 300 43 57 400 23 33Formulation C 100 50 67 200 75 96 300 85 99 400 94 100 Formulation J 10040 75 200 73 94 300 93 98 400 95 99 49-01 100 63 77 200 67 94 300 77 99400 88 96 49-02 100 63 75 200 83 88 300 93 98 400 95 99 49-03 100 67 75200 82 95 300 95 99 400 98 99 49-04 100 60 75 200 82 97 300 96 99 400 98100 49-05 100 63 73 200 75 89 300 80 98 400 87 97 49-06 100 58 63 200 7893 300 93 99 400 98 100 49-07 100 60 67 200 78 93 300 93 99 400 100 9949-08 100 missing missing 200 missing missing 300 78 95 400 98 99 49-09100 23 30 200 65 83 300 80 98 400 93 99 49-10 100 65 67 200 83 95 300 9799 400 99 99 49-11 100 72 73 200 90 98 300 96 97 400 99 99 49-12 100 6863 200 90 92 300 98 99 400 97 99 49-13 100 43 73 200 72 87 300 83 98 40093 96 49-14 100 62 77 200 78 99 300 95 99 400 98 100 49-15 100 52 60 20078 93 300 94 98 400 97 99 49-16 100 38 68 200 68 99 300 87 97 400 94 9949-17 100 55 75 200 68 91 300 83 96 400 87 98

Herbicidal effectiveness exceeding that of commercial standardcomposition J, at least on ABUTH, was recorded with severalcompositions, including 49-02 (steareth-20 plus butyl stearate), 49-03(ceteareth-20 plus butyl stearate), 49-04 (ceteareth-15 plus butylstearate), 49-10 (steareth-20 plus methyl palmitate), 49-11(ceteareth-20 plus methyl palmitate) and 49-12 (ceteareth-15 plus methylpalmitate). Compositions lacking fatty acid ester performed slightlyless well overall than those containing butyl stearate or methylpalmitate.

Example 50

Spray compositions were prepared containing glyphosate IPA salt andexcipient ingredients as shown in Table 50a. Compositions were preparedby simple mixing of ingredients. Soybean lecithin (45% phospholipid,Avanti), where included, was first prepared with sonication in water tomake a homogeneous composition. Four different concentrations ofglyphosate (not shown in Table 50a) were prepared, calculated toprovide, when applied in a spray volume of 93 l/ha, the glyphosate ratesshown in Table 50b.

TABLE 50a % w/w Spray Fluorad Butyl Methyl Oleth- Lecithin Methyl oleatecomp. Lecithin FC-754 stearate oleate 20 supplied as supplied as 50-010.05 0.050 soybean lecithin 50-02 0.05 0.050 soybean lecithin 50-03 0.05soybean lecithin 50-04 0.050 50-05 0.050 50-06 0.05 LI-700 50-07 0.0050.05 50-08 0.01 0.05 50-09 0.05 50-10 0.005 50-11 0.01 pure 50-12 0.01methylated seed oil

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and Prickly side (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH and ECHCFand 21 days after planting SIDSP. Evaluation of herbicidal inhibitionwas done 14 days after application.

Formulations B and C were applied as comparative treatments,representing technical glyphosate IPA salt and a commercial formulationof glyphosphate IPA salt respectively. Results, averaged for allreplicates of each treatment, are shown in Table 50b.

TABLE 50b Glyphosate rate % Inhibition Spray composition g a.e./ha ABUTHECHCF SIDSP Formulation B 50 0 0 0 (technical) 100 38 35 35 200 87 50 90300 95 88 94 Formulation C 50 0 2 0 (commercial) 100 32 55 25 200 85 9793 300 96 99 96 50-01 50 78 53 88 100 90 60 95 200 99 96 99 300 99 97 9850-02 50 25 15 43 100 72 30 82 200 94 62 93 300 95 77 94 50-03 50 20 832 100 52 22 78 200 87 55 91 300 95 65 93 50-04 50 62 37 85 100 82 68 92200 97 96 95 300 98 95 97 50-05 50 15 IO 25 100 47 27 23 200 85 62 87300 90 63 92 50-06 50 0 2 0 100 20 15 20 200 85 60 82 300 90 65 90 50-0750 67 27 82 100 87 55 93 200 94 92 96 300 97 99 97 50-08 50 62 30 75 10078 63 91 200 93 96 96 300 94 98 98 50-09 50 65 45 77 100 80 73 95 200 9398 97 300 95 99 99 50-10 50 10 25 5 100 23 35 37 200 90 50 93 300 92 7394 50-11 50 10 25 0 100 52 33 43 200 88 72 93 300 94 78 94 50-12 50 0 150 100 43 35 33 200 91 70 90 300 94 82 93

Results of this test using glyphosate as the exogenous chemical aresummarized as follows:

Butyl stearate along at 0.05% (50-05) did not greatly enhanceeffectiveness.

The combination of lecithin and butyl stearate (50-02) gave surprisinglystrong enhancement of effectiveness, suggesting a synergisticinteraction between these two excipient substances.

Oleth-20 at the low concentration of 0.05% (50-09) gave extremely higheffectiveness, superior to that obtained with the commercial standard.Addition of 0.005% butyl stearate (50-07) or 0.01% methyl oleate (50-08)did not provide further enhancement.

Example 51

Spray compositions were prepared containing paraquat dichloride andexcipient ingredients. Compositions 51-01 to 51-12 were exactly likecompositions 50-01 to 50-12 except that a different active ingredientwas used and a range of active ingredient concentrations was selectedappropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly sida (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH, 8 daysafter planting ECHCF and 21 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 12 days after application.

Standards included technical paraquat dichloride and Gramoxone, acommercial formulation of paraquat from Zeneca. Results, averaged forall replicates of each treatment, are shown in Table 51.

TABLE 51 Paraquat rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Paraquat dichloride 25 50 83 55 (technical) 50 57 78 60 10073 84 69 200 85 95 99 Gramoxone 25 40 72 40 (commercial) 50 60 70 52 10072 58 55 200 72 89 63 51-01 25 75 93 67 50 82 97 91 100 95 98 97 200 10099 99 51-02 25 67 80 48 50 68 87 65 100 88 97 93 200 96 99 98 51-03 2555 65 42 50 62 87 65 100 83 96 93 200 95 99 97 51-04 25 53 82 45 50 6394 53 100 88 99 86 200 92 99 98 51-05 25 58 67 50 50 60 62 45 100 70 7362 200 85 90 88 51-06 25 53 77 43 50 60 92 40 100 80 93 55 200 96 99 7851-07 25 65 80 45 50 82 92 70 100 96 96 89 200 100 98 99 51-08 25 67 8037 50 82 90 71 100 97 98 65 200 99 99 93 51-09 25 72 90 50 50 80 97 57100 91 99 94 200 97 100 97 51-10 25 67 87 45 50 68 75 57 100 78 93 63200 82 97 82 51-11 25 65 80 45 50 73 77 62 100 90 95 62 200 94 98 7851-12 25 67 78 37 50 75 90 55 100 77 97 90 200 85 99 92

Results of this test using paraquat as the exogenous chemical aresummarized as follows:

Butyl stearate along at 0.05% (51-05) did not enhance effectiveness.

The combination of lecithin and butyl stearate (51-02) gave surprisinglystrong enhancement of effectiveness, suggesting a synergisticinteraction between these two excipient substances.

Oleth-20 at the low concentration of 0.05% (51-09) gave extremely higheffectiveness, superior to that obtained with the commercial standard.Addition of 0.005% butyl stearate (51-07) or 0.01% methyl oleate (51-08)did not provide further enhancement.

Example 52

Spray compositions were prepared containing acifluorfen sodium salt andexcipient ingredients. Compositions 52-01 to 52-12 were exactly likecompositions 50-01 to 50-12 respectively except that a different activeingredient was used and a range of active ingredient concentrations wasselected appropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly sida (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 15 days after planting ABUTH, 9 daysafter planting ECHCF and 22 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 10 days after application.

Standards included technical acifluorfen sodium and Blazer, a compoundformulation of acifluorfen from Rohm & Haas. Results, averaged for allreplicates of each treatment, are shown in Table 52.

TABLE 52 Acifluorfen rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Acifluorfen 25 20 2 15 (technical) 50 32 7 17 100 52 18 35200 62 35 40 Blazer 25 30 30 5 (commercial) 50 53 53 12 100 55 55 7 20065 65 32 52-01 25 60 7 20 50 63 20 20 100 65 43 33 200 80 70 48 52-02 2525 7 5 50 42 12 25 100 60 30 22 200 68 68 50 52-03 25 22 5 10 50 55 7 33100 62 25 27 200 65 55 48 52-04 25 57 7 13 50 67 10 32 100 67 35 32 20070 70 45 52-05 25 30 3 15 50 47 27 27 100 55 42 37 200 65 60 38 52-06 2528 0 3 50 50 0 i0 100 55 30 25 200 67 58 47 52-07 25 35 20 17 50 55 3527 100 58 63 32 200 67 67 55 52-08 25 40 20 8 50 57 30 28 100 60 60 30200 70 77 48 52-09 25 47 20 22 50 55 35 35 100 62 65 38 200 68 82 5052-10 25 28 0 5 50 48 0 10 100 53 5 25 200 62 35 40 52-11 25 35 0 5 5043 0 30 100 50 0 35 200 65 43 47 52-12 25 40 5 5 50 55 18 35 100 60 4738 200 70 62 48

Results of this test using acifluorfen as the exogenous chemical aresummarized as follows:

Butyl stearate at 0.05% alone (52-05) and in combination with lecithin(52-02) enhanced efectiveness, particularly on ECHCF.

Oleth-20 at the low concentration of 0.05% (52-09) gave effectivenesssuperior to that obtained with the commercial standard. Addition of0.005% butyl stearate (52-07) or 0.01% methyl oleate (52-08) did notprovide further enhancement.

Example 53

Spray compositions were prepared containing asulam and excipientingredients. Compositions 53-01 to 53-12 were exactly like compositions50-01 to 50-12 respectively except that a different active ingredientwas used and a range of active ingredient concentration was selectedappropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly sida (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Application ofspray concentrations were made 14 days after planting ABUTH, 11 daysafter planting ECHCF and 21 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 14 days after application.

Standards included technical asulam and Asulox, a commercial formulationof asulam from Rhône-Poulenc. Results, averaged for all replicates ofeach treatment, are shown in Table 53.

TABLE 53 Asulam rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Asulam 200 0 12 0 (technical) 400 17 27 5 800 48 32 20 140042 50 37 Asulox 200 3 5 0 (commercial) 400 27 30 20 800 52 45 25 1400 5060 40 53-01 200 5 8 13 400 23 45 22 800 50 50 30 1400 60 65 48 53-02 2000 20 17 400 33 40 20 800 47 48 33 1400 53 68 55 53-03 200 3 20 3 400 2852 7 800 50 50 23 1400 50 58 43 53-04 200 3 40 7 400 35 45 18 800 52 5025 1400 58 60 42 53-05 200 0 10 3 400 23 30 18 800 33 50 32 1400 45 5738 53-06 200 2 30 10 400 8 47 17 800 50 55 28 1400 52 63 40 53-07 200 043 3 400 22 48 17 800 40 55 28 1400 52 60 33 53-08 200 7 47 22 400 20 4822 800 53 55 30 1400 57 60 33 53-09 200 0 45 7 400 25 50 7 800 53 60 321400 55 63 37 53-10 200 22 37 10 400 27 45 I0 800 50 43 23 1400 52 52 2753-11 200 25 33 5 400 15 37 13 800 48 42 25 1400 42 52 28 53-12 200 3 2517 400 13 42 18 800 50 45 30 1400 52 50 33

Results of this test using asulam as the exogenous chemical aresummarized as follows:

Butyl stearate alone at 0.05% (53-05) enhanced effectiveness on ECHCF.

The combination of lecithin and butyl stearate (53-02) gave greaterenhancement of effectiveness than either excipient substance alone.

Oleth-20 at the low concentration of 0.05% (53-09) gave, at lowexogenous chemical rates, effectiveness on ECHCF superior to thatobtained with the commercial standard. Addition of 0.005% butyl stearate(53-07) or 0.01% methyl oleate (53-08) did not provide furtherenhancement.

Example 54

Spray compositions were prepared containing dicamba sodiums salt andexcipient ingredients. Compositions 54-01 to 54-12 were exactly likecompositions 50-01 to 50-12 respectively except that a different activeingredient was used and a range of active ingredient concentrations wasselected appropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly sida (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH, 8 daysafter planting ECHCF and 21 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 17 days after application.

Standards included technical dicamba sodium and Banvel, a commercialformulation of dicamba from Sandoz. Results, averaged for all replicatesof each treatment, are shown in Table 54.

TABLE 54 Dicamba rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SDSP Dicamba 25 47 0 30 (technical) 50 63 0 40 100 82 0 50 200 935 58 Banvel 25 47 0 35 (commercial) 50 68 0 40 100 91 0 53 200 93 3 6354-01 25 42 0 38 50 67 0 48 100 92 0 67 200 93 3 73 54-02 25 43 0 43 5058 0 50 100 85 0 62 200 89 8 72 54-03 25 50 0 32 50 65 0 45 100 90 0 60200 94 13 68 54-04 25 43 0 35 50 65 0 42 100 94 0 s3 200 94 13 67 54-0525 50 0 35 50 68 0 40 100 88 0 53 200 92 15 60 54-06 25 40 0 40 50 65 045 100 88 0 52 200 92 8 70 54-07 25 45 0 42 50 57 0 45 100 88 0 62 20088 20 68 54-08 25 40 0 38 50 62 0 45 100 97 18 62 200 93 17 73 54-09 2533 0 35 50 60 0 45 100 93 0 63 200 96 15 73 54-10 25 35 0 30 50 57 0 43100 90 0 50 200 90 3 70 54-11 25 45 0 30 50 53 0 42 100 89 0 55 200 92 073 54-12 25 38 0 37 50 60 0 45 100 96 0 52 200 93 0 70

Results of this test using dicamba as the exogenous chemical aresummarized as follows:

Butyl stearate alone at 0.05% (54-05) provided slight enhancement ofeffectiveness.

The combination of lecithin and butyl stearate (54-02) gave greaterenhancement of effectiveness on SIDSP than either of these two excipientsubstances alone.

Oleth-20 at the low concentration of 0.05% (54-09) gave effectiveness onSIDSP superior to that obtained with the commercial standard. Additionof 0.005% butyl stearate (54-07) or 0.01% methyl oleate (54-08) did notprovide significant further enhancement.

Example 55

Spray compositions were prepared containing metsulfuron-methyl andexcipient ingredients. Compositions 55-01 to 55-12 were exactly likecompositions 50-01 to 50-12 respectively except that a different activeingredient was used as a range of active ingredient concentrations wasselected appropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly side (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH, 8 daysafter planting ECHCF and 21 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 14 days after application.

Standards included technical metsulfuron-methyl and Ally, a commercialformulation of metsulfuron from Du Pont. Results, averaged for allreplicates of each treatment, are shown in Table 55.

TABLE 55 Metsulfuron rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Metsulfuron 0.5 72 0 5 (technical) 1 90 0 23 5 96 0 50 10 9730 55 Ally 0.5 75 0 5 (commercial) 1 85 0 22 5 95 0 42 10 97 25 53 55-010.5 95 0 47 1 96 20 53 5 97 25 62 10 98 45 62 55-02 0.5 87 0 40 1 90 1055 5 95 10 58 10 96 40 63 55-03 0.5 87 0 27 1 90 0 40 5 96 10 57 10 9733 63 55-04 0.5 90 0 33 1 95 10 50 5 98 17 62 10 99 28 58 55-05 0.5 85 027 1 90 0 33 5 95 0 47 10 95 13 60 55-06 0.5 77 0 30 1 89 10 47 5 96 1762 10 98 33 60 55-07 0.5 94 0 55 1 97 10 60 5 98 43 60 I0 97 55 65 55-080.5 93 0 55 1 96 5 58 5 97 42 60 97 50 60 65 55-09 0.5 93 0 55 1 97 1062 5 98 55 62 10 98 65 63 55-10 0.5 85 0 28 I 82 0 30 5 95 10 52 10 9617 57 55-11 0.5 73 0 25 1 88 20 28 5 94 25 53 10 96 32 57 55-12 0.5 75 032 1 85 20 37 5 94 23 55 10 96 25 57

Results of this test using metsulfuron as the exogenous chemical aresummarized as follows:

Butyl stearate alone at 0.05% (55-05) enhanced effectiveness to a levelsuperior to that obtained with the commercial standard.

The combination of lecithin and butyl stearate (55-02) gave greaterenhancement of effectiveness than was obtained with either of these twoexcipient substances alone.

Oleth-20 at the low concentrations of 0.05% (55-09) gave higheffectiveness, superior to that obtained with the commercial standard.Addition of 0.005% butyl stearate (55-07) or 0.01% methyl oleate (55-08)did not provide further enhancement.

Example 56

Spray compositions were prepared containing imazethapyr and excipientingredients Compositions 56-01 to 56-12 were exactly like compositions50-01 to 50-12 respectively except that a different active ingredientwas used and a range of active ingredient concentrations was selectedappropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly sida (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH, 14 daysafter planting ECHCF and 21 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 14 days after application.

Standards included technical imazethapyr and Pursuit, a commercialformulation of imazethapyr from American Cyanamid. Results, averaged forall replicates of each treatment, are shown in Table 56.

TABLE 56 Imazethapyr rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Imazethapyr 5 78 5 20 (technical) 10 83 20 30 25 93 35 40 5094 53 50 Pursuit 5 70 5 25 (commercial) 10 73 33 30 25 90 50 42 50 93 6257 56-01 5 70 45 35 10 75 62 52 25 92 63 57 50 93 72 62 56-02 5 73 57 3210 75 67 43 25 90 70 52 50 92 72 57 56-03 5 70 42 27 10 78 42 35 25 9053 45 50 92 62 52 56-04 5 73 55 33 10 77 68 45 25 93 68 47 50 94 68 6056-05 5 73 47 32 10 73 45 40 25 90 62 47 50 91 68 52 56-06 5 78 72 30 1083 70 35 25 93 77 62 50 94 78 58 56-07 5 82 75 38 10 90 90 52 25 93 9353 50 97 97 62 56-08 5 75 77 38 10 90 92 50 25 95 93 57 50 97 99 6356-09 5 78 80 40 10 83 89 63 25 93 93 62 50 96 93 60 56-10 5 85 50 37 1077 50 45 25 91 63 48 50 93 75 57 56-11 5 75 38 43 10 80 38 37 25 92 6245 50 93 73 53 56-12 5 75 55 38 10 83 60 43 25 92 67 53 50 93 77 55

Results of this test using imazethapyr as the exogenous chemical aresummarized as follows:

Butyl stearate alone at 0.05% (56-05) significantly enhancedeffectiveness on ECHCF and slightly on SDISP.

The combination of lecithin and butyl stearate (56-02) gave enhancementof effectiveness on ECHCF greater than that obtained with either ofthese two excipient substances alone.

Oleth-20 at the low concentration of 0.05% (56-09) gave extremely higheffectiveness, greatly superior to that obtained with the commercialstandard, especially on ECHCF. Addition of 0.005 % butyl stearate(56-07) further enhanced performance of low exogenous chemical rates onABUTH more effectively than addition of 0.01% methyl oleate (56-08).

Example 57

Spray compositions were prepared containing fluazifop-p-butyl andexcipient ingredients. Compositions 57-01 to 57-12 were exactly likecompositions 50-01 to 50-12 respectively except that a different activeingredient was used and a range of active ingredient concentrations wasselected appropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and broadleaf signalgrass (Brachiaria platyphylla,BRAPP) plants were grown and treated by the standard procedures givenabove. Applications of spray compositions were made 15 days afterplanting ABUTH, 15 days after planting ECHCF and 16 days after BRAPP.Evaluation of herbicidal inhibition was done 10 days after application.

Standards included technical fluazifop-p-butyl and Fusilade 5, acommercial formulation of fluazifop-p-butyl from Zeneca. Results,averaged for all replicates of each treatment, are shown in Table 57.

TABLE 57 Fluazifop-p rate % Inhibition Spray composition g a.i./ha ABUTHECHCF BRAPP Fluazifop-p-butyl 2 0 0 20 (technical) 5 0 3 35 15 5 45 6530 5 57 78 Fusilade 5 2 0 0 27 (commercial) 5 0 27 33 15 5 52 78 30 7 7585 57-01 2 0 0 20 5 2 27 30 15 5 58 78 30 10 87 83 57-02 2 0 7 25 5 0 3530 15 2 58 75 30 8 78 75 57-03 2 0 0 18 5 0 8 27 15 0 45 75 30 0 55 7557-04 2 0 20 32 5 2 42 25 15 2 55 72 30 5 80 78 57-05 2 0 13 32 5 2 4232 15 2 55 72 30 7 58 73 57-06 2 2 17 23 5 0 20 25 15 0 50 75 30 0 73 7757-07 2 0 50 40 5 0 52 60 15 0 67 80 30 0 92 85 57-08 2 0 43 35 5 0 5537 15 7 88 82 30 3 96 85 57-09 2 0 47 18 5 0 50 35 15 0 80 80 30 3 93 8557-10 2 0 23 5 0 37 42 15 5 55 75 30 10 58 80 57-11 2 0 7 10 5 0 30 2815 0 50 62 30 12 53 68 57-12 2 0 5 20 5 0 7 35 15 5 48 68 30 12 60 77

Results of this test using fluazifop-p-butyl as the exogenous chemicalare summarized as follows:

Butyl stearate alone at 0.05% (57-05) and in combination with lecithin(57-02) enhanced effectiveness, especially on ECHCF.

Oleth-20 at the low concentration of 0.05% (57-09) gave extremely higheffectiveness on ECHCF, superior to that obtained with the commercialstandard. Addition of 0.005% butyl stearate (57-07) or 0.01% methyloleate (57-08) did not provide significant further enhancement.

Example 58

Spray compositions were prepared containing alachlor and excipientingredients. Compositions 58-01 to 58-12 were exactly like compositions50-01 to 50-12 respectively except that a different active ingredientwas used and a range of active ingredient concentrations was selectedappropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly sida (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH, 8 daysafter planting ECHCF and 14 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 9 days after application.

Standards included technical alachlor and Lasso, a commercialformulation of alachlor from Monsanto Company. Results, averaged for allreplicates of each treatment, are shown in Table 58.

TABLE 58 Alachlor rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Alachlor 500 0 0 0 (technical) 1000 0 0 0 2000 0 0 0 4000 00 0 Lasso 500 0 0 0 (commercial) 1000 0 5 13 2000 0 30 17 4000 15 43 6558-01 500 0 0 0 1000 0 0 0 2000 0 0 0 4000 10 0 7 58-02 500 0 0 0 1000 00 0 2000 0 22 7 4000 12 47 12 58-03 500 0 0 0 1000 0 0 0 2000 0 0 0 400010 0 0 58-04 500 0 0 0 1000 0 0 0 2000 0 0 0 4000 5 0 15 58-05 500 0 0 01000 0 0 0 2000 0 0 0 4000 3 0 5 58-06 500 0 0 0 1000 0 0 0 2000 0 13 74000 0 37 12 58-07 500 0 0 0 1000 0 8 0 2000 0 28 15 4000 12 50 20 58-08500 0 0 0 1000 0 8 0 2000 0 8 0 4000 5 20 5 58-09 500 0 0 0 1000 0 0 02000 0 3 0 4000 12 42 32 58-10 500 0 0 0 1000 0 0 0 2000 0 0 0 4000 0 00 58-11 500 0 0 0 1000 0 0 0 2000 0 0 0 4000 0 0 0 58-12 500 0 0 0 10000 0 0 2000 0 0 0 4000 0 0 0

None of the compositions tested enhanced post-emergence foliar-appliedherbicidal effectiveness of alachlor in this test. Alachlor is not knownas a foliar-applied herbicide.

Example 59

Spray compositions were prepared containing glufosinate ammonium saltand excipient ingredients. Compositions 59-01 to 59-12 were exactly likecompositions 50-01 to 50-12 respectively except that a different activeingredient was used and a range of active ingredient concentrations wasselected appropriate to the active ingredient being applied.

Velvetleaf (Abutilon theophrasti, ABUTH), Japanese millet (Echinochloacrus-galli, ECHCF) and prickly side (Sida spinosa, SIDSP) plants weregrown and treated by the standard procedures given above. Applicationsof spray compositions were made 14 days after planting ABUTH, 10 daysafter planting ECHCF and 17 days after planting SIDSP. Evaluation ofherbicidal inhibition was done 11 days after application.

Standards included technical glufosinate ammonium and Liberty, acommercial formulation of glufosinate from AgrEvo. Results, averaged forall replicates of each treatment, are shown in Table 59.

TABLE 59 Glufosinate rate % Inhibition Spray composition g a.i./ha ABUTHECHCF SIDSP Glufosinate 50 0 0 5 (technical) 100 47 0 10 300 90 23 96600 98 43 94 Liberty 50 77 70 20 (commercial) 100 88 96 93 300 98 100 97600 99 100 99 59-01 50 77 33 70 100 95 58 93 300 98 95 97 600 99 99 9859-02 50 33 30 50 100 63 32 93 300 96 52 90 600 98 96 97 59-03 50 15 3038 100 50 33 87 300 92 40 94 600 98 70 98 59-04 50 92 47 50 100 90 53 85300 98 98 96 600 98 99 98 59-05 50 35 20 20 100 37 30 20 300 97 45 78600 91 53 92 59-06 50 10 0 20 100 20 3 20 300 89 47 82 600 91 94 8959-07 50 50 35 70 100 73 52 80 300 95 87 98 600 98 98 97 59-08 50 48 3088 100 83 50 93 300 98 97 96 600 98 99 96 59-09 50 58 35 92 100 91 62 93300 98 96 97 600 98 99 96 59-10 50 30 30 0 100 43 35 10 300 96 43 92 60095 70 91 59-11 50 33 35 0 100 53 35 7 300 96 43 89 600 97 88 93 59-12 5037 5 5 100 37 20 10 300 95 40 88 600 97 85 93

Results of this test using glufosinate as the exogenous chemical aresummarized as follows:

Butyl stearate alone at 0.05% (59-05) enhanced effectiveness on ECHCF.

The combination of lecithin and butyl stearate (59-02) gave greaterenhancement of effectiveness than either of these two excipientsubstances alone.

Oleth-20 at the low concentrations of 0.05% (59-09) gave extremely higheffectiveness, superior on SIDSP to that obtained with the commercialstandard. Addition of 0.005% butyl stearate (59-07) or 0.01% methyloleate (59-08) did not provide further enhancement.

Example 60

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 60a. Concentratecompositions 60-01 to 60-12 and 60-16 are oil-in-water emulsions andwere prepared by process (vii). Concentrate composition 60-13 is anaqueous solution concentrate and was prepared by process (viii).

TABLE 60a Gly- Concentrate phosate % w/w Type of Type of composition ga.e./l Oil Surfactant oil surfactant 60-01 163 0.5 5.0 butyl stearatesteareth-30 60-02 163 0.5 5.0 methyl stearate steareth-30 60-03 163 0.55.0 butyl stearate Neodol 44-13 60-04 163 0.5 5.0 methyl stearate Neodol44-13 60-05 163 0.5 5.0 butyl stearate ceteareth-15 60-06 163 0.5 5.0methyl stearate ceteareth-15 60-07 163 0.5 5.0 butyl stearate laureth-2360-08 163 0.5 5.0 butyl stearate oleth-20 60-09 163 0.5 5.0 butylstearate steareth-20 60-10 163 0.5 5.0 butyl stearate ceteareth-27 60-11163 0.3 5.0 butyl stearate ceteareth-27 60-12 163 0.3 2.5 butyl stearateceteareth-27 60-13 163 5.0 none ceteareth-27 60-14 163 0.5 5.0 methylstearate ceteareth-27 60-15 163 0.5 5.0 methyl stearate steareth-2060-16 163 0.5 5.0 methyl stearate oleth-20

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray concentrationswere made 20 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 16 days after application.

Formulations B, C and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 60b.

TABLE 60b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 45 57 200 35 53 300 50 57 400 38 33Formulation C 100 70 98 200 90 99 300 97 100 400 100 100 Formulation J100 72 88 200 93 99 300 97 99 400 98 99 60-01 100 83 97 200 97 100 30099 100 400 100 100 60-02 100 80 99 200 96 100 300 99 100 400 99 10060-03 100 73 98 200 92 100 300 98 99 400 99 100 60-04 100 73 98 200 8799 300 97 99 400 99 100 60-05 100 80 98 200 87 100 300 98 100 400 100100 60-06 100 78 97 200 95 98 300 98 100 400 99 100 60-07 100 78 98 20088 100 300 96 100 400 98 100 60-08 100 75 98 200 93 99 300 97 99 400 10099 60-09 100 83 93 200 95 100 300 98 100 400 100 100 60-10 100 80 97 20095 98 300 98 99 400 100 100 60-11 100 80 97 200 93 99 300 98 100 400 10099 60-12 100 77 93 200 88 100 300 99 100 400 99 100 60-13 100 80 73 20095 95 300 99 100 400 100 100 60-14 100 77 94 200 92 99 300 98 100 400100 99 60-15 100 78 92 200 94 99 300 98 100 400 99 100 60-16 100 77 93200 90 98 300 98 99 400 99 100

Extremely high herbicidal effectiveness was provided by ceteareth-27(composition 60-13); this was further enhanced by addition of a smallamount of butyl stearate (60-10, 60-11) or methyl stearate (60-14).Compositions performing better than commercial standard Formulations Cand J, at least on ABUTH, included those containing steareth-30,steareth-20 or ceteareth-27; in this test oleth-20 was not quite aseffective as these standard alkylethers.

Example 61

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 61a. Concentratecomposition 61-17 is an oil-in-water emulsion and was prepared byprocess (vii). Concentrate compositions 61-01 to 61-16 and 61-18 wereprepared by process (x) using soybean lecithin (45% phospholipid,Avanti).

TABLE 61a % w/w Concentrate Glyphosate Butyl Ethomeen Ceteareth-Ceteareth- composition g a.e./l Lecithin stearate T/25 20 27 61-01 2200.75 0.75 1.5 61-02 220 0.75 0.75 1.5 61-03 220 0.75 0.75 3.0 61-04 2200.75 7.5O I.5 61-05 220 0.75 7.50 3.0 61-06 220 3.75 3.75 3.0 61-07 2201.50 1.50 3.0 61-08 220 1.50 1.50 1.5 61-09 220 3.75 3.75 1.5 1.5 61-10220 1.50 1.50 1.5 1.5 61-11 220 3.75 7.50 1.5 1.5 61-12 220 3.75 1.50I.5 1.5 61-13 220 0.75 3.75 I.5 1.5 61-14 220 0.75 7.50 I.5 1.5 61-15220 0.75 3.75 3.0 3.0 61-16 220 0.75 7.50 3.0 3.0 61-17 220 7.50 3.061-18 220 0.75 7.50 3.0

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 23 days after planting ABUTH and ECHCF, and evaluation ofberbicidal inhibition was done 18 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 61b.

TABLE 61b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 12 62 200 5 55 300 23 63 400 43 78Formulation J 100 27 82 200 62 98 300 88 95 400 96 99 61-01 100 13 79200 68 95 300 82 99 400 95 91 61-02 100 27 82 200 60 97 300 81 95 400 8799 61-03 100 37 77 200 62 96 300 78 98 400 89 90 61-04 100 37 84 200 5795 300 84 99 400 89 100 61-05 100 33 77 200 65 100 300 78 97 400 88 9761-06 100 43 78 200 62 95 300 87 97 400 95 96 61-07 100 48 78 200 80 91300 90 99 400 76 93 61-08 100 48 83 200 67 89 300 86 96 400 93 97 61-09100 62 84 200 82 98 300 85 99 400 91 97 61-10 100 63 80 200 75 96 300 8599 400 99 99 61-11 100 42 75 200 78 98 300 92 99 400 93 100 61-12 100 5280 200 73 93 300 86 99 400 97 97 61-13 100 55 83 200 75 97 300 97 99 40092 99 61-14 100 52 87 200 73 95 300 91 97 400 87 98 61-15 100 57 83 20092 96 300 98 100 400 100 98 61-16 100 79 88 200 87 97 300 99 99 400 9794 61-17 100 58 83 200 47 94 300 88 98 400 91 93 61-18 100 58 87 200 7591 300 83 99 400 91 98

Outstanding herbicidal effectiveness was provided by composition 61-18,containing lecithin, ceteareth-27 and butyl stearate. Addition of 3%Ethomeen T/25 (61-16) further enhanced effectiveness. Slightly reducedeffectiveness at the lowest glyphosate rate was observed on ABUTH whenthe butyl stearate concentration was cut in half (61-15).

Example 62

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 62a. Concentratecompositions 62-01 to 62-04, 62-06, 62-08, 62-10 and 62-18 areoil-in-water emulsions and were prepared by process (vii). Concentratecompositions 62-05, 62-07 and 62-09 are aqueous solution concentratesand were prepared by process (viii). Concentrate compositions 62-11 to62-17 contain colloidal particulates and were prepared by process (ix).

The compositions of this example all showed acceptable storagestability. The compositions shown as containing colloidal particulatewere not storage-stable unless the colloidal particulate was included asshown.

TABLE 62a Gly % w/w Concentrate phosate Butyl Aerosil Type ofcomposition g a.e./l stearate Surfactant 380 surfactant 62-01 163 0.55.0 steareth-20 62-02 163 0.5 5.0 ceteareth-27 62-03 163 0.5 5.0oleth-20 62-04 163 0.5 5.0 ceteth-20 62-05 163 5.0 ceteth-20 62-06 1630.5 5.0 Neodol 44-13 62-07 163 5.0 Neodol 44-13 62-08 163 0.5 5.0ceteareth-15 62-09 163 5.0 ceteareth-15 62-10 163 0.5 5.0 steareth-3062-11 360 1.0 10.0 1.25 ceteth-20 62-12 360 1.0 10.0 1.25 Neodol 44-1362-13 360 1.0 10.0 1.25 ceteareth-15 62-14 360 1.0 10.0 1.25 steareth-3062-15 360 1.0 10.0 1.25 steareth-20 62-16 360 1.0 10.0 1.25 oleth-2062-17 360 1.0 10.0 1.25 ceteareth-27 62-18 163 0.5 5.0 laureth-23

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 22 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulation B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 62b.

TABLE 62b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 0 30 200 2 60 300 17 75 400 50 73Formulation J 100 20 63 200 42 98 300 75 100 400 83 98 62-01 100 27 57200 67 98 300 80 99 400 87 98 62-02 100 27 63 200 53 87 300 77 99 400 8799 62-03 100 12 50 200 53 99 300 65 100 400 83 99 62-04 100 20 63 200 5098 300 73 98 400 87 98 62-05 100 18 70 200 57 93 300 80 99 400 83 9962-06 100 17 63 200 35 95 300 60 100 400 75 100 62-07 100 3 43 200 43 95300 62 100 400 68 96 62-08 100 20 43 200 43 88 300 75 99 400 80 97 62-09100 37 57 200 55 93 300 83 100 400 83 99 62-10 100 37 50 200 60 96 30083 99 400 88 99 62-11 100 8 37 200 37 93 300 68 99 400 70 97 62-12 10013 43 200 40 91 300 67 100 400 77 96 62-13 100 25 40 200 40 80 300 62 97400 78 98 62-14 100 23 33 200 37 86 300 75 99 400 78 94 62-15 100 23 30200 43 78 300 53 93 400 78 98 62-16 100 23 37 200 37 95 300 63 97 400 7895 62-17 100 18 50 200 45 88 300 75 69 400 73 93 62-18 100 missingmissing 200 missing missing 300 missing missing 400 missing missing

Compositions exhibiting herbicidal effectiveness greater than thatprovided by commercial standard Formulation J included 62-01(steareth-20 plus butyl stearate), 62-09 (ceteareth-15) and 62-10(steareth-20 plus butyl stearate).

Example 63

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 63a. All areoil-in-water emulsions and were prepared by process (vii).

TABLE 63a % w/w Concentrate Glyphosate Butyl Type of composition ga.e./l stearate Surfactant surfactant 63-01 163 1.00 10.0 laureth-2363-02 163 0.50 5.0 laureth-23 63-03 163 0.25 2.5 laureth-23 63-04 1631.00 10.0 Neodol 1-9 63-05 163 0.50 5.0 Neodol 1-9 63-06 163 0.25 2.5Neodol 1-9 63-07 163 1.00 10.0 steareth-10 63-08 163 0.50 5.0steareth-10 63-09 163 0.25 2.5 steareth-10 63-10 163 0.50 5.0steareth-20 63-11 163 0.25 2.5 steareth-20 63-12 163 0.25 1.0steareth-20 63-13 163 0.50 5.0 oleth-20 63-14 163 0.25 2.5 oleth-2063-15 163 0.25 1.0 oleth-20 63-16 163 0.50 5.0 ceteareth-27 63-17 1630.25 2.5 ceteareth-27 63-18 163 0.25 1.0 ceteareth-27

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 21 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 20 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatments, are shown in Table 63b.

TABLE 63b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 0 42 200 0 43 300 23 50 400 0 28Formulation J 100 0 73 200 57 85 300 68 93 400 87 94 63-01 100 18 75 20058 92 300 85 90 400 94 95 63-02 100 3 77 200 47 90 300 65 89 400 87 9563-03 100 13 80 200 53 88 300 72 98 400 82 99 63-04 100 0 0 200 53 88300 67 95 400 83 95 63-05 100 2 60 200 50 83 300 70 93 400 85 92 63-06100 0 52 200 55 83 300 62 96 400 77 98 63-07 100 8 70 200 68 95 300 9199 400 95 100 63-08 100 10 65 200 67 99 300 78 99 400 93 100 63-09 100 580 200 52 98 300 75 100 400 86 98 63-10 100 0 65 200 62 84 300 58 94 40075 100 63-11 100 5 83 200 50 99 300 63 97 400 87 99 63-12 100 10 76 20060 96 300 72 100 400 100 100 63-13 100 20 85 200 67 100 300 91 100 40096 98 63-14 100 23 68 200 62 89 300 80 100 400 99 99 63-15 100 5 57 20055 93 300 89 95 400 90 98 63-16 100 30 68 200 68 94 300 83 98 400 100100 63-17 100 43 68 200 62 99 300 78 100 400 100 99 63-18 100 25 52 20053 84 300 85 94 400 98 95

Compositions having a 1:3 or lower weight/weight ratio of surfactant toglyphosate a.e., yet outperforming commercial standard Formulation J atleast on ABUTH in this test, included those containing just 1%alkylether surfactant (ratio about 1:15) together with 0.25% butylstearate, where the alkylether surfactant was steareth-20 (63-12),oleth-20 (63-15) or ceteareth-27 (63-18).

Example 64

Dry granular concentrate compositions were prepared containingglyphosate ammonium salt and excipient ingredients as shown in Table64a. The preparation procedure was as follows. Ammonium glyphosatepowder was added to a blender. Excipient ingredients were slowly added,together with sufficient water to wet the powder and form a stiff dough.The blender was operated for sufficient time to thoroughly mix allingredients. The dough was then transferred to extrusion apparatus andwas extruded to form granules, which were finally dried in a fluid beddryer.

TABLE 64a % w/w Type of Conc. Glyphosate Butyl Colloidal Type ofcolloidal comp. a.e. Lecithin stearate Surfactant particulate surfactantparticulate 64-01 68.7 21.0 steareth-20 64-02 66.0 2.2 22.0 steareth-2064-03 66.1 24.0 oleth-20 64-04 66.0 2.2 22.0 oleth-20 64-05 67.9 10.02.0 10.0 MON 0818 64-06 59.2 10.0 20.0 + 2.0 FC-754 + MON 0818 64-0768.0 21.0 0.8 tallowamine 20EO Aerosil 90 64-08 68.0 21.0 0.8tallowamine 20EO Aluminum oxide C 64-09 66.1 24.0 ceteth-20 64-10 66.02.2 22.0 ceteth-20 64-11 71.2 16.1 2.0 ceteth-20 Aerosil 380 64-12 71.116.3 1.0 ceteth-20 Aerosil blend (*) 64-13 71.2 16.1 2.0 steareth-20Aerosil 380 64-14 71.2 16.1 1.0 steareth-20 Aerosil blend (*) 64-15 68.020.0 1.9 oleth-20 Aerosil-380 64-16 70.8 16.6 1.0 oleth-20 Aerosil blend(*) (*) Aerosil MOX-80 + Aerosil MOX-170 (1:1)

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 21 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 20 days after application.

Formulations J and K were applied as comparative treatments. Results,averaged for all replicates of each treatments, are shown in Table 64b.

TABLE 64b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation J 100 52 80 200 90 96 300 96 100 400 97 99Formulation K 100 33 70 200 67 93 300 83 99 400 93 100 64-01 100 47 60200 87 98 300 97 98 400 100 98 64-02 100 47 63 200 80 94 300 90 99 40098 100 64-03 100 62 62 200 83 93 300 97 96 400 97 100 64-04 100 47 57200 78 94 300 87 100 400 98 100 64-05 100 25 53 200 60 88 300 80 97 40083 98 64-06 100 35 37 200 65 62 300 83 83 400 90 95 64-07 100 63 55 20072 97 300 83 100 400 94 100 64-08 100 30 65 200 72 94 300 87 100 400 9299 64-09 100 37 63 200 77 83 300 88 99 400 97 99 64-10 100 40 55 200 8393 300 94 96 400 98 99 64-11 100 42 55 200 78 94 300 88 92 400 94 9964-12 100 38 58 200 78 97 300 92 97 400 95 100 64-13 100 25 50 200 80 88300 96 95 400 98 98 64-14 100 50 53 200 88 92 300 98 99 400 99 99 64-15100 33 57 200 75. 91 300 94 97 400 98 99 64-16 100 33 55 200 77 90 30088 99 400 96 100

Several dry granular compositions of this Example outperformedcommercial standard composition K, at least on AUBTH. They included64-01 to 64-04 and 64-10 to 64-16, all containing an alkylethersurfactant (steareth-20, oleth-20 or ceteth-20).

Example 65

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 65a. All were preparedby process (x) using soybean lecithin (45% phospholipid, Avanti), exceptthat compositions 65-09 and 65-10 were processed by ultrasonicationinstead of by use of a microfluidizer as indicated in the column ofTable 65a headed “Process”.

TABLE 65a % w/w Conc. Glyphosate Butyl Ethomeen MON Ceteareth-Ceteareth- Process comp. g a.e./l Lecithin stearate T/25 0818 20 27 (*)65-01 220 0.75 3.75 3.0 3.0 B 65-02 220 0.75 0.75 3.0 3.0 B 65-03 2200.75 3.75 3.0 3.0 B 65-04 220 0.75 0.75 3.0 3.0 B 65-05 220 6.00 1.503.0 3.0 B 65-06 220 6.00 1.50 3.0 3.0 B 65-07 220 4.00 1.00 3.0 3.0 B65-08 220 4.00 1.00 3.0 3.0 B 65-09 220 0.75 3.75 3.0 3.0 A 65-10 2200.75 0.75 3.0 3.0 A 65-11 220 0.75 3.75 6.0 B 65-12 220 0.75 3.75 6.0 B65-13 345 6.00 1.50 4.5 4.5 B 65-14 345 6.00 1.50 6.0 3.0 B 65-15 3456.00 1.50 6.0 6.0 B 65-16 345 0.50 7.50 12.0 B 65-17 345 6.00 1.50 4.54.5 3.0 B (*) Process: A Ultrasonicated B Microfluidized, 3 cycles

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 19 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 15 days after application.

Formulation B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 65b.

TABLE 65b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 150 45 82 250 55 71 350 80 72 450 88 77Formulation J 150 55 83 250 89 88 350 97 93 450 99 93 550 99 87 65-01150 92 83 250 96 96 350 99 96 450 100 86 65-02 150 85 93 250 97 78 35097 90 450 99 90 65-03 150 87 85 250 98 92 350 99 95 450 100 95 65-04 15087 89 250 97 92 350 99 94 450 99 91 65-05 150 87 77 250 98 89 350 99 93450 99 84 65-06 150 12 18 250 96 73 350 99 85 450 99 84 65-07 150 82 89250 88 96 350 96 98 450 97 97 65-08 150 88 94 250 95 90 350 99 98 450 9998 65-09 150 94 94 250 95 100 350 97 99 450 99 98 65-10 150 94 94 250 9899 350 99 97 450 99 96 65-11 150 83 81 250 94 88 350 98 93 450 99 9965-12 150 68 79 250 95 96 350 98 100 450 99 98 65-13 150 86 98 250 95 98350 99 100 450 100 98 65-14 150 85 98 250 98 98 350 99 98 450 100 9865-15 150 86 95 250 97 97 350 99 95 450 100 96 65-16 150 93 94 250 98 98350 99 98 450 100 97 65-17 150 95 96 250 98 100 350 100 100 450 100 98

Many compositions containing lecithin and butyl stearate outperformedcommercial standard Formulation J in this test.

Example 66

Aqueous and dry granular concentrate compositions were prepared as shownin Table 66a. Dry granular concentrate compositions 66-01 to 66-11contain glyphosate ammonium salt, and were prepared by the processdescribed in Example 64.

Aqueous concentrate compositions 66-12 to 66-16 contain glyphosate IPAsalt and were prepared by process (v) using soybean lecithin (45%phospholipid, Avanti).

TABLE 66a % w/w Type of Conc. Glyphosate Glyphosate Butyl Colloidal Typeof colloidal comp. g a.e./l a.e. Lecithin stearate Surfactantparticulate surfactant particulate 66-01 68.7 21.0 steareth-20 66-0266.1 24.0 oleth-20 66-03 67.9 10.0 2.0 10.0 MON 0818 66-04 59.2 10.020.0 + 2.0 FC-754 + MON 0818 66-05 66.1 24.0 ceteth-20 66-06 71.2 16.12.0 steareth-20 Aerosil 380 66-07 71.2 16.1 2.0 steareth-20 Aerosilblend 66-08 68.0 20.0 1.9 oleth-20 Aerosil 380 66-09 63.5 25.0 2.0steareth-20 Aerosil blend 66-10 67.9 20.0 2.0 steareth-20 Aerosil blend66-11 72.2 15.0 2.0 steareth-20 Aerosil blend 66-12 370 4.7  4.7steareth-20 66-13 350 4.9  4.9 ceteareth-27 66-14 348 5.0  5.0ceteareth-15 66-15 348 5.0  5.0 oleth-20 66-16 351 4.4  5.0 steareth-30Aerosil blend: Aerosil MOX-80 + Aerosil MOX-170 (1:1)

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 20 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 16 days after application.

Formulations J and K were applied as comparative treatments. Results,averaged for all replicates of each treatments, are shown in Table 66b.

TABLE 66b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation J 100 0 20 200 28 57 300 58 96 400 73 99Formulation K 100 22 13 200 42 83 300 48 91 400 58 95 66-01 100 28 30200 48 80 300 80 97 400 85 99 66-02 100 43 52 200 68 80 300 72 88 400 8694 66-03 100 23 37 200 50 83 300 75 88 400 85 96 66-04 100 50 45 200 7380 300 85 92 400 95 94 66-05 100 18 45 200 65 83 300 87 95 400 94 8666-06 100 47 50 200 62 68 300 82 94 400 91 87 66-07 100 50 47 200 60 78300 87 87 400 93 93 66-08 100 30 55 200 55 77 300 82 85 400 88 97 66-09100 45 50 200 57 78 300 83 83 400 84 89 66-10 100 42 50 200 57 80 300 7391 400 91 90 66-11 100 28 48 200 50 75 300 70 87 400 82 89 66-12 100 2040 200 63 80 300 67 96 400 80 88 66-13 100 27 35 200 50 85 300 77 90 40084 86 66-14 100 27 25 200 40 70 300 68 94 400 89 91 66-15 100 17 20 20047 82 300 58 89 400 91 95 66-16 100 22 20 200 41 80 300 84 89 400 99 98

All compositions of the invention in this study exhibited greaterherbicidal effectiveness on both ABUTH and ECHCF, in some cases by avery substantial margin, than commercial standard Formulation K.

Example 67

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 67a. Concentratecompositions 67-01 to 67-07, 67-17 and 67-18 were prepared by process(v). Concentrate compositions 67-08 to 67-15 were prepared by process(x). Concentrate compositions 67-16 was prepared by process (viii).

TABLE 67a % w/w Conc. Glyphosate Fluorad Butyl Ethomeen Arcosolve comp.g a.e./l Lecithin FC-754 stearate T/25 Ceteareth-20 DPM Ceteareth-2767-01 348 3.0 3.00 0.75 67-02 348 3.8 3.75 5.00 67-03 348 3.8 3.75 7.5067-04 348 2.0 5.00 0.75 67-05 348 5.0 5.00 0.75 67-06 348 2.0 2.00 67-07348 1.0 1.00 67-08 220 1.5 1.5 3.00 3.0 67-09 220 1.5 1.5 3.00 3.0 67-10220 1.5 1.5 6.00 3.0 67-11 220 1.5 1.5 6.00 3.0 67-12 220 3.0 1.5 3.003.0 67-13 220 3.0 1.5 3.00 3.0 67-14 348 1.5 1.5 6.00 3.0 67-15 348 3.01.5 3.00 3.0 67-16 348 3.00 67-17 348 3.0 3.0 67-18 348 5.0 13.00  5.0

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 18 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatment, are shown in Table 67b.

TABLE 67b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 28 32 200 41 37 300 73 64 400 22 30Formulation J 100 38 32 200 82 73 300 89 91 400 97 89 67-01 100 73 28200 90 66 300 97 92 400 100 96 67-02 100 77 32 200 87 67 300 84 78 40098 84 67-03 100 79 33 200 82 66 300 99 81 400 97 88 67-04 100 69 35 20095 59 300 96 84 400 92 91 67-05 100 82 32 200 92 55 300 96 71 400 94 8767-06 100 83 33 200 100 52 300 100 68 400 99 75 67-07 100 77 35 200 9058 300 95 71 400 94 90 67-08 100 51 40 200 89 75 300 96 92 400 95 9867-09 100 76 57 200 98 81 300 97 86 400 96 98 67-10 100 69 60 200 98 63300 95 82 400 99 90 67-11 100 61 60 200 94 84 300 97 89 400 99 97 67-12100 64 53 200 95 82 300 96 90 400 95 98 67-13 100 61 58 200 94 78 300 8887 400 100 94 67-14 100 56 61 200 88 77 300 91 82 400 97 89 67-15 100 4252 200 82 80 300 86 90 400 97 92 67-16 100 64 49 200 86 75 300 97 88 400100 82 67-17 100 57 32 200 88 66 300 95 73 400 100 88 67-18 100 52 35200 70 77 300 82 79 400 97 73

Compositions 67-08 to 67-15, containing lecithin, butyl stearate,Ethomeen T/25 and a C₁₆₋₁₈ alkylether surfactant (ceteareth-20 orceteareth-27) exhibited a very high degree of herbicidal effectiveness.Not only was performance, at least of 67-08 to 67-13, on ABUTHsubstantially better than that of Formulation J, these compositionsperformed considerably better than Formulation J on ECHCF as well.

Example 68

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 68a. All containcolloidal particulates and were prepared by process (ix).

The compositions of this example all showed acceptable storagestability. The compositions shown as containing colloidal particulatewere not storage-stable unless the colloidal particulate was included asshown.

TABLE 68a % w/w Conc. Glyphosate Aerosil Type of Type of comp. g a.e./lOil Surfactant 380 oil surfactant 68-01 360 1.0 10.0 1.25 butyl stearateoleth-20 68-02 360 1.0 10.0 1.25 stearylamine oleth-20 68-03 360 1.010.0 1.25 stearyl alcohol oleth-20 68-04 360 1.0 10.0 1.25 docosaneoleth-20 68-05 360 10.0 1.25 none oleth-20 68-06 360 1.0 10.0 1.25 butylstearate steareth-30 68-07 360 1.0 10.0 1.25 stearylamine steareth-3068-08 360 1.0 10.0 1.25 stearyl alcohol steareth-30 68-09 360 1.0 10.01.25 docosane steareth-30 68-10 360 10.0 1.25 none steareth-30 68-11 3605.0 + 5.0 1.25 none oleth-20 + steareth-20 68-12 360 5.0 + 5.0 1.25 noneoleth-20 + steareth-30 68-13 360 5.0 + 5.0 1.25 none oleth-20 +ceteareth-27 68-14 360 5.0 + 5.0 1.25 none oleth-20 + ceteareth-15 68-15360 5.0 + 5.0 1.25 none steareth-30 + steareth-20 68-16 360 5.0 + 5.01.25 none steareth-30 + ceteareth-27 68-17 360 5.0 + 5.0 1.25 nonesteareth-30 + ceteareth-15 68-18 360 10.0 1.25 none laureth-23

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 19 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatments, as shown in Table 68b.

TABLE 68b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 0 60 200 15 73 300 33 88 400 57 91Formulation J 100 5 70 200 37 92 300 80 99 400 77 96 68-01 100 13 88 20032 85 300 48 98 400 90 93 68-02 100 10 70 200 45 98 300 72 99 400 80 9868-03 100 3 77 200 25 94 300 47 98 400 75 99 68-04 100 7 67 200 23 94300 40 99 400 7 47 68-05 100 7 76 200 25 88 300 45 96 400 75 97 68-06100 12 96 200 30 97 300 45 98 400 15 60 68-07 100 8 83 200 12 97 300 3594 400 50 98 68-08 100 15 72 200 30 88 300 40 99 400 0 33 68-09 100 5 73200 15 94 300 47 99 400 5 53 68-10 100 7 79 200 15 95 300 45 98 400 6299 68-11 100 5 84 200 13 98 300 30 98 400 55 100 68-12 100 3 95 200 1799 300 28 99 400 67 100 68-13 100 5 90 200 17 99 300 30 100 400 60 9868-14 100 3 98 200 25 97 300 38 100 400 57 100 68-15 100 5 97 200 25 97300 40 100 400 40 99 68-16 100 10 97 200 15 98 300 52 100 400 0 47 68-17100 7 97 200 25 94 300 40 98 400 33 97 68-18 100 7 96 200 25 99 300 55100 400 73 100

Percent inhibition data for the 400 g a.e./ha glyphosate rate in thistest are unreliable and should be ignored. Neither oleth-20 (composition68-05) nor steareth-20 (68-10) provided herbicidal effectiveness equalto Formulation J in this study, and no great or consistent furtherenhancement was obtained by adding butyl stearate.

Example 69

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 69a. Concentratecompositions 69-01 to 69-03 are oil-in-water emulsions and were preparedby process (vii). Compositions 69-04 to 69-18 all contain particulatesand were prepared by process (ix). Different mixing methods wereemployed in the final stage preparation of these compositions, asindicated in the column of Table 69a headed “Process”.

The compositions of this example all showed acceptable storagestability. The compositions shown as containing colloidal particulatewere not storage-stable unless the colloidal particulate was included asshown.

TABLE 69a % w/w Concentrate Glyphosate Butyl Aerosil Type of Processcomposition g a.e./l stearate Surfactant 380 surfactant (*) 69-01 1630.5 5.0 oleth-20 69-02 163 0.5 5.0 steareth-20 69-03 163 0.5 5.0ceteareth-27 69-04 360 1.0 10.0 1.25 ceteareth-15 A 69-05 360 1.0 10.01.25 ceteth-20 A 69-06 360 1.0 10.0 1.25 steareth-20 A 69-07 360 1.010.0 1.25 oleth-20 A 69-08 360 1.0 10.0 1.25 ceteareth-27 A 69-09 3601.0 10.0 1.25 steareth-30 A 69-10 360 10.0 1.25 steareth-30 A 69-11 3601.0 10.0 1.25 oleth-20 A 69-12 360 1.0 10.0 1.25 oleth-20 B 69-13 3601.0 10.0 1.25 oleth-20 C 69-14 360 1.0 10.0 1.25 oleth-20 D 69-15 3601.0 10.0 1.25 oleth-20 E 69-16 360 1.0 10.0 1.25 oleth-20 F 69-17 3601.0 10.0 1.25 oleth-20 G 69-18 360 1.0 10.0 1.25 oleth-20 A (*) Process:A Silverson mixer, medium screen, 3 minutes at 7000 rpm B Silversonmixer, coarse screen, 3 minutes at 7000 rpm C Fann mixer, 50% output, 5minutes D Turrax mixer, 3 minutes at 8000 rpm E Overhead stirrer, lowspeed F Overhead stirrer, high speed G Hand shaking, 3 minutes

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Applications of spray compositions weremade 17 days after planting ABUTH and ECHCF, and evaluation ofherbicidal inhibition was done 19 days after application.

Formulations B and J were applied as comparative treatments. Results,averaged for all replicates of each treatments, are shown in Table 69b.

TABLE 69b Glyphosate rate % Inhibition Concentrate composition g a.e./haABUTH ECHCF Formulation B 100 20 40 200 45 50 300 65 72 400 78 85Formulation J 100 43 53 200 80 80 300 96 82 400 99 94 69-01 100 45 57200 80 72 300 89 78 400 98 83 69-02 100 53 57 200 80 78 300 89 77 400 9383 69-03 100 45 60 200 83 75 300 97 73 400 97 85 69-04 100 45 45 200 8080 300 83 83 400 95 95 69-05 100 42 42 200 77 77 300 93 93 400 98 9869-06 100 30 30 200 42 42 300 27 30 400 3 20 69-07 100 40 40 200 77 75300 90 93 400 97 86 69-08 100 43 50 200 80 80 300 92 93 400 96 98 69-09100 0 2 200 82 75 300 83 96 400 90 88 69-10 100 57 60 200 80 70 300 8888 400 95 93 69-11 100 35 47 200 72 75 300 80 75 400 85 77 69-12 100 4747 200 72 77 300 80 90 400 86 78 69-13 100 55 50 200 75 83 300 78 92 40091 92 69-14 100 52 50 200 75 78 300 83 88 400 99 92 69-15 100 47 47 20070 73 300 87 87 400 75 63 69-16 100 43 40 200 78 75 300 88 88 400 87 9169-17 100 43 43 200 67 88 300 80 75 400 92 83 69-18 100 27 40 200 63 57300 82 73 400 87 70

Results obtained with compositions 69-06 are out of line with other datain this Example and an error in formulation or application is suspected.Some differences in herbicidal effectiveness were evident when acompositions containing 360 g a.e./I glyphosate, 1% butyl stearate, 10%oleth-20 and 1.25% Aerosil 380 was processed in different ways (69-11 to69-17). However, as compositions 69-07 and 69-11 were identicallyprocessed yet differed in effectiveness, no firm conclusions can bedrawn from this test.

Example 70

Aqueous concentrate compositions were prepared containing glyphosate IPAsalt and excipient ingredients as shown in Table 70a. All containcolloidal particulates and were prepared by process (ix).

The compositions of this example all showed acceptable storagestability. The compositions shown as containing colloidal particulatewere not storage-stable unless the colloidal particulate was included asshown.

TABLE 70a % w/w Concentrate Glyphosate Type of Type of composition a.e.Oil Surfactant Aerosil 380 oil surfactant 70-01 31 1.0 10.0 1.25 Butylstearate steareth-20 70-02 31 1.0 10.0 1.25 Butyl stearate oleth-2070-03 31 1.0 10.0 1.25 Butyl stearate steareth-30 70-04 31 10.0 1.25none steareth-30

Velvetleaf (Abutilon theophrasti, ABUTH) and Japanese millet(Echinochloa crus-galli, ECHCF) plants were grown and treated by thestandard procedures given above. Treatments were applied at fourdifferent hours of the day. Applications of spray compositions were made16 days after planting ABUTH and ECHCF, and evaluation of herbicidalinhibition was done 22 days after application.

Formulation J was applied as a comparative treatment. Results, averagedfor all replicates of each treatments, are shown in Table 70b.

TABLE 70b Concentrate Hour when Glyphosate rate % Inhibition compositionapplied g a.e./ha ABUTH ECHCF Formulation J 1000 100 5 33 200 42 75 30067 83 400 77 93 70-01 1000 100 7 33 200 40 70 300 50 82 400 78 91 70-021000 100 18 33 200 37 73 300 48 91 400 80 92 70-03 1000 100 30 33 200 4075 300 82 85 400 83 80 70-04 1000 100 30 30 200 43 78 300 78 92 400 9395 Formulation J 1200 100 5 38 200 35 87 300 53 96 400 88 99 70-01 1200100 10 30 200 47 91 300 70 89 400 78 97 70-02 1200 100 5 37 200 40 75300 48 87 400 70 94 70-03 1200 100 20 37 200 50 82 300 78 98 400 83 9770-04 1200 100 33 33 200 45 93 300 75 98 400 95 100 Formulation J 1400100 15 40 200 30 90 300 55 100 400 80 100 70-01 1400 100 17 40 200 45 70300 75 97 400 80 98 70-02 1400 100 17 47 200 35 83 300 67 97 400 63 9770-03 1400 100 30 40 200 63 80 300 77 97 400 78 100 70-04 1400 100 23 40200 45 87 300 73 100 400 78 100 Formulation J 1600 100 10 37 200 32 83300 52 97 400 75 98 70-01 1600 100 27 43 200 40 89 300 77 99 400 95 9970-02 1600 100 20 53 200 40 95 300 53 98 400 80 98 70-03 1600 100 27 60200 60 93 300 78 97 400 96 100 70-04 1600 100 15 37 200 43 83 300 67 97400 78 96

Compositions 70-03 illustrates the consistency of high-level performanceobtainable with, in this case, steareth-30 at an approximately 1:3weight/weight ratio to glyphosate a.e., together with a small amount ofbutyl stearate and Aerosil 380. An average of percent inhibition ofABUTH across all four glyphosate rates shows the following comparison of70-03 with Formulation J, applied at four different hours of the day:

Hour Formulation J Composition 70-03 1000 48 59 1200 45 58 1400 48 621600 42 65

The preceding description of specific embodiments of the presentinvention is not intended to be a complete list of every possibleembodiment of the invention. Persons skilled in this field willrecognize that modifications can be made to the specific embodimentsdescribed here that would be within the scope of the present invention.

What is claimed is:
 1. A plant treatment composition comprising (a) anexogenous chemical; a first excipient substance which is a propyl,isopropyl or butyl ester of a C₁₂₋₁₈ fatty acid; and (c) a secondexcipient substance which is an amphiphilic substance having a criticalpacking parameter greater than ⅓ and which is a liposome-formingmaterial, wherein the weight/weight ratio of first excipient substanceto the exogenous chemical is from about 1:3 to about 1:100, and theweight/weight ratio of second excipient substance to the exogenouschemical is from about 1:3 to about 1:100.
 2. The composition of claim 1wherein R¹⁴ is saturated in from about 40 to 100 percent by weight ofall compounds having the stated formula present in the composition. 3.The composition of claim 1 wherein the first excipient substance isbutyl stearate.
 4. The composition of claim 1 wherein the exogenouschemical is a foliar-applied exogenous chemical.
 5. The composition ofclaim 4 wherein the exogenous chemical is a pesticide, gametocide orplant growth regulator.
 6. The composition of claim 5 wherein theexogenous chemical is a herbicide, nematicide or plant growth regulator.7. The composition of claim 6 wherein the exogenous chemical is aherbicide.
 8. The composition of claim 7 wherein the herbicide isselected from the group consisting of acetanilides, bipyridyls,cyclohexenones, dinitroanilines, diphenylethers, fatty acids,hydroxybenzonitriles, imidazolinones, phenoxies, phenoxypropionates,substituted ureas, sulfonylureas, thiocarbamates and triazines.
 9. Thecompositions of claim 7 wherein the herbicide is selected from the groupconsisting of acetochlor, alachlor, metolachlor, aminotriazole, asulam,bentazon, bialaphos, diquat, paraquat, bromacil, clethodim, sethoxydim,dicamba, diflufenican, pendimethalin, acifluorfen, C₉₋₁₀ fatty acids,fomesafen, oxyfluorfen, fosamine, flupoxam, glufosinate, glyphosate,bromoxynil, imazaquin, imazethapyr, isoxaben, norflurazon, 2,4-D,diclofop, fluazifop, quizalofop, picloram, propanil, fluometuron,isoproturon, chlorimuron, chlorsulfuron, halosulfuron, metsulfuron,primisulfuron, sulfometuron, sulfosulfuron, triallate, atrazine,metribuzin, triclopyr, and herbicidal derivatives thereof.
 10. Thecomposition of claim 9 wherein the herbicide is glyphosate or aherbicidal derivative thereof.
 11. The composition of claim 10 whereinthe herbicide is glyphosate in its acid form.
 12. The composition ofclaim 6 wherein the exogenous chemical is water-soluble.
 13. Thecomposition of claim 12 wherein the exogenous chemical is a salt havingan anion portion and a cation portion.
 14. The composition of claim 13wherein at least one of said anion and cation portions is biologicallyactive and has a molecular weight of less than about
 300. 15. Thecomposition of claim 14 wherein the exogenous chemical is paraquat ordiquat.
 16. The composition of claim 14 wherein the exogenous chemicalexhibits systemic biological activity in the plant.
 17. The compositionof claim 16 wherein the exogenous chemical has one or more functionalgroups selected from the group consisting of amine, amide, caboxylate,phosphonate and phosphinate groups.
 18. The composition of claim 17wherein the exogenous chemical is a salt of 3,4,4-trifluoro-3-butenoicacid or of N-(3,4,4-trifluoro-1-oxo-3-butenyl)glycine that exhibitsnematicidal activity.
 19. The composition of claim 17 wherein theexogenous chemical is a herbicidal or plant growth regulating compoundhaving at least one of each of amine, carboxylate and either phosphonateor phosphinate functional groups.
 20. The composition of claim 19wherein the herbicidal or plant growth regulating compound is a salt ofglufosinate.
 21. The composition of claim 20 wherein the salt ofglufosinate is the ammonium salt.
 22. The composition of claim 19wherein the herbicidal or plant growth regulating compound is a salt ofN-phosphonomethylglycine.
 23. The composition of claim 22 wherein thesalt of N-phosphonomethylglycine is selected from the group consistingof sodium, potassium, ammonium, mono-, di-, tri- andtetra-C₁₋₄-alkylammonium, mono-, di- and tri-C₁₋₄-alkanolammonium, mono-di- and tri-C₁₋₄-alkylsulfonium and sulfoxonium salts.
 24. Thecomposition of claim 23 wherein the salt of N-phosphonomethylglycine isthe ammonium, monoisopropylammonium or trimethylsulfonium salt.
 25. Thecomposition of claim 1, wherein the second excipient substance comprisesan amphiphilic compound or mixture of such compounds having twohydrophobic moieties, each of which is a saturated alkyl or acyl grouphaving from about 8 to about 22 carbon atoms; wherein said amphiphiliccompound or mixture of such compounds having said two hydrophobicmoieties constitutes from about 40 to 100 percent by weight of allamphiphilic compounds having two hydrophobic moieties present in saidliposome-forming material.
 26. The composition of claim 25, wherein thesecond excipient substance has a hydrophilic head group comprising acationic group.
 27. The composition of claim 26, wherein the cationicgroup is an amine group.
 28. The composition of claim 1, wherein thesecond excipient substance comprises a liposome-forming compound havinga hydrophobic moiety comprising two independently saturated orunsaturated hydrocarbyl groups R¹ and R² each independently having about7 to about 21 carbon atoms, said liposome-forming compound having aformula selected from the group consisting of: (a)N⁺(CH₂R¹)(CH₂R²)(R³)(R⁴)Z⁻ wherein R³ and R⁴ are independently hydrogen,C₁₋₄ alkyl or C₁₋₄ hydroxyalkyl and Z is a suitable anion; (b)N⁺(R⁵)(R⁶)(R⁷)CH₂CH(OCH₂R¹)CH₂(OCH₂R²)Z⁻ wherein R⁵, R⁶ and R⁷ areindependently hydrogen, C₁₋₄ alkyl or C₁₋₄ hydroxyalkyl and Z is asuitable anion; (c) N⁺(R⁵)(R⁶)(R⁷)CH₂CH(OCOR¹)CH₂(OCOR²)Z⁻ wherein R⁵,R⁶, R⁷ and Z are as defined above; and (d)N⁺(R⁵)(R⁶)(R⁷)CH₂CH₂OPO(O⁻)OCH₂CH(OCOR¹)CH₂(OCOR²) wherein R5, R6, andR7 are as defined above.
 29. The composition of claim 28, wherein Z isselected from the group consisting of hydroxide, chloride, bromide,iodide, sulfate, phosphate and acetate.
 30. The composition of claim 28,wherein R¹ and R² are independently saturated straight-chain alkylgroups each having about 7 to about 21 carbon atoms.
 31. The compositionof claim 28, wherein the second excipient substance is a phospholipidselected from the group consisting ofdi-C₈₋₂₂-alkanoylphosphatidylcholines anddi-C₈₋₂₂-alkanoylphosphatidylethanolamines.
 32. The composition of claim31, wherein the second excipient substance is a dipalmitoyl ordistearoyl ester of phosphatidylcholine or a mixture thereof.
 33. Thecomposition of claim 1, further comprising water in an amount effectiveto make the composition a dilute aqueous composition ready forapplication to foliage of a plant.
 34. The composition of claim 1,wherein the composition is a shelf-stable concentrate compositioncomprising the exogenous chemical in an amount of about 15 to about 90percent by weight.
 35. The composition of claim 34, wherein thecomposition is a solid composition comprising the exogenous chemicalsubstance in an amount of about 30 to about 90 percent by weight. 36.The composition of claim 35, wherein the composition is a water-solubleor water-dispersible granular formulation.
 37. The composition of claim34, further comprising a liquid diluent, and wherein the compositioncomprises the exogenous chemical substance in an amount of about 15 toabout 60 percent by weight.
 38. The composition of claim 37 wherein theexogenous chemical substance is water-soluble and is present in anaqueous phase of the composition in an amount of about 15 to about 45percent by weight of the composition.
 39. The composition of claim 38,wherein the composition is an emulsion having an oil phase and the firstexcipient substance is present predominantly in the oil phase.
 40. Thecomposition of claim 39, wherein the composition is an oil-in-wateremulsion.
 41. The composition of claim 39, wherein the composition is awater-in-oil emulsion.
 42. The composition of claim 39, wherein thecomposition is a water-in-oil-in-water multiple emulsion.
 43. Thecomposition of claim 39, further comprising a solid inorganicparticulate colloidal material.
 44. The composition of claim 43, whereinthe colloidal material comprises particles having an average surfacearea of about 50 to about 400 m²/g.
 45. The composition of claim 43,wherein the colloidal material comprises particles having an averagesurface area of about 180 to about 400 m²/g.
 46. The composition ofclaim 43, wherein the colloidal material comprises particles of aninorganic oxide selected from the oxide of silicon, aluminum andtitanium.
 47. A plant treatment method, comprising contacting foliage ofa plant with a biologically effective amount of a composition accordingto any of claims 1, through
 33. 48. A plant treatment method, comprisingthe steps of (a) contacting foliage of a plant with a biologicallyeffective amount of an exogenous chemical; and contacting the samefoliage with an aqueous composition that comprises (i) a first excipientsubstance which is propyl, isopropyl or butyl ester of a C₁₂₋₁₈ fattyacid, and (ii) a second excipient substance having a critical packingparameter greater than ⅓ and which is a liposome-forming material;wherein the weight/weight ratio of first excipient substance to theexogenous chemical is from about 1:3 to about 1:100, the weight/weightratio of second excipient substance to the exogenous chemical is fromabout 1:3 to about 1:100, and step (b) occurs simultaneously with orwithin about 96 hours before or after step (a).